diff --git a/app/assets/tailwind/application.css b/app/assets/tailwind/application.css
index 1a0c15cf..cb3d5852 100644
--- a/app/assets/tailwind/application.css
+++ b/app/assets/tailwind/application.css
@@ -166,7 +166,6 @@
     background: #a6a6a6;
   }
 }
-/* The following Markdown CSS has been removed as requested */
 
 .mt-safe {
 	margin-top: env(safe-area-inset-top);
diff --git a/app/assets/tailwind/maybe-design-system.css b/app/assets/tailwind/maybe-design-system.css
index f8379818..72e52292 100644
--- a/app/assets/tailwind/maybe-design-system.css
+++ b/app/assets/tailwind/maybe-design-system.css
@@ -217,6 +217,18 @@
   --shadow-md: 0px 4px 8px -2px --alpha(var(--color-black) / 6%);
   --shadow-lg: 0px 12px 16px -4px --alpha(var(--color-black) / 6%);
   --shadow-xl: 0px 20px 24px -4px --alpha(var(--color-black) / 6%);
+
+  --animate-stroke-fill: stroke-fill 3s 300ms forwards;
+
+  @keyframes stroke-fill {
+    0% {
+      stroke-dashoffset: 43.9822971503;
+    }
+
+    100% {
+      stroke-dashoffset: 0;
+    }
+  }
 }
 
 /* Custom shadow borders used for surfaces / containers  */
@@ -504,7 +516,7 @@
 @layer components {
   /* Buttons */
   .btn {
-    @apply px-3 py-2 rounded-lg text-sm font-medium cursor-pointer disabled:cursor-not-allowed focus:outline-gray-500;
+    @apply inline-flex items-center gap-2 px-3 py-2 rounded-lg text-sm font-medium cursor-pointer disabled:cursor-not-allowed focus:outline-gray-500;
     @apply transition-all duration-300;
   }
 
@@ -548,6 +560,14 @@
     }
   }
 
+  .btn--outline-destructive {
+    @apply border border-red-500 text-red-500 hover:bg-gray-50;
+
+    @variant theme-dark {
+      @apply border-red-400 text-red-400 hover:button-bg-destructive-hover;
+    }
+  }
+
   .btn--destructive {
     @apply button-bg-destructive text-white hover:button-bg-destructive-hover disabled:button-bg-disabled disabled:hover:button-bg-disabled disabled:text-red-400;
 
diff --git a/app/controllers/accounts_controller.rb b/app/controllers/accounts_controller.rb
index 33b3980a..f003ab31 100644
--- a/app/controllers/accounts_controller.rb
+++ b/app/controllers/accounts_controller.rb
@@ -31,7 +31,7 @@ class AccountsController < ApplicationController
       family.sync_later
     end
 
-    redirect_to accounts_path
+    redirect_back_or_to accounts_path
   end
 
   private
diff --git a/app/controllers/application_controller.rb b/app/controllers/application_controller.rb
index 70895a3c..cebfea1f 100644
--- a/app/controllers/application_controller.rb
+++ b/app/controllers/application_controller.rb
@@ -1,5 +1,5 @@
 class ApplicationController < ActionController::Base
-  include Onboardable, Localize, AutoSync, Authentication, Invitable, SelfHostable, StoreLocation, Impersonatable, Breadcrumbable, FeatureGuardable
+  include Onboardable, Localize, AutoSync, Authentication, Invitable, SelfHostable, StoreLocation, Impersonatable, Breadcrumbable, FeatureGuardable, Notifiable
   include Pagy::Backend
 
   helper_method :require_upgrade?, :subscription_pending?
diff --git a/app/controllers/categories_controller.rb b/app/controllers/categories_controller.rb
index 04ffb0e5..b1516f86 100644
--- a/app/controllers/categories_controller.rb
+++ b/app/controllers/categories_controller.rb
@@ -56,8 +56,13 @@ class CategoriesController < ApplicationController
     redirect_back_or_to categories_path, notice: t(".success")
   end
 
+  def destroy_all
+    Current.family.categories.destroy_all
+    redirect_back_or_to categories_path, notice: "All categories deleted"
+  end
+
   def bootstrap
-    Current.family.categories.bootstrap_defaults
+    Current.family.categories.bootstrap!
 
     redirect_back_or_to categories_path, notice: t(".success")
   end
diff --git a/app/controllers/concerns/accountable_resource.rb b/app/controllers/concerns/accountable_resource.rb
index d7d3b169..16fdbebd 100644
--- a/app/controllers/concerns/accountable_resource.rb
+++ b/app/controllers/concerns/accountable_resource.rb
@@ -37,11 +37,15 @@ module AccountableResource
 
   def create
     @account = Current.family.accounts.create_and_sync(account_params.except(:return_to))
+    @account.lock_saved_attributes!
+
     redirect_to account_params[:return_to].presence || @account, notice: t("accounts.create.success", type: accountable_type.name.underscore.humanize)
   end
 
   def update
     @account.update_with_sync!(account_params.except(:return_to))
+    @account.lock_saved_attributes!
+
     redirect_back_or_to @account, notice: t("accounts.update.success", type: accountable_type.name.underscore.humanize)
   end
 
diff --git a/app/controllers/concerns/notifiable.rb b/app/controllers/concerns/notifiable.rb
new file mode 100644
index 00000000..0d8ea384
--- /dev/null
+++ b/app/controllers/concerns/notifiable.rb
@@ -0,0 +1,58 @@
+module Notifiable
+  extend ActiveSupport::Concern
+
+  included do
+    helper_method :render_flash_notifications
+    helper_method :flash_notification_stream_items
+  end
+
+  private
+    def render_flash_notifications
+      notifications = flash.flat_map { |type, data| resolve_notifications(type, data) }.compact
+
+      view_context.safe_join(
+        notifications.map { |notification| view_context.render(**notification) }
+      )
+    end
+
+    def flash_notification_stream_items
+      items = flash.flat_map do |type, data|
+        notifications = resolve_notifications(type, data)
+
+        if type == "cta"
+          notifications.map { |notification| turbo_stream.replace("cta", **notification) }
+        else
+          notifications.map { |notification| turbo_stream.append("notification-tray", **notification) }
+        end
+      end.compact
+
+      # If rendering flash notifications via stream, we mark them as used to avoid
+      # them being rendered again on the next page load
+      flash.clear
+
+      items
+    end
+
+    def resolve_cta(cta)
+      case cta[:type]
+      when "category_rule"
+        { partial: "rules/category_rule_cta", locals: { cta: } }
+      end
+    end
+
+    def resolve_notifications(type, data)
+      case type
+      when "alert"
+        [ { partial: "shared/notifications/alert", locals: { message: data } } ]
+      when "cta"
+        [ resolve_cta(data) ]
+      when "loading"
+        [ { partial: "shared/notifications/loading", locals: { message: data } } ]
+      when "notice"
+        messages = Array(data)
+        messages.map { |message| { partial: "shared/notifications/notice", locals: { message: message } } }
+      else
+        []
+      end
+    end
+end
diff --git a/app/controllers/family_merchants_controller.rb b/app/controllers/family_merchants_controller.rb
new file mode 100644
index 00000000..01531a47
--- /dev/null
+++ b/app/controllers/family_merchants_controller.rb
@@ -0,0 +1,54 @@
+class FamilyMerchantsController < ApplicationController
+  before_action :set_merchant, only: %i[edit update destroy]
+
+  def index
+    @breadcrumbs = [ [ "Home", root_path ], [ "Merchants", nil ] ]
+
+    @merchants = Current.family.merchants.alphabetically
+
+    render layout: "settings"
+  end
+
+  def new
+    @merchant = FamilyMerchant.new(family: Current.family)
+  end
+
+  def create
+    @merchant = FamilyMerchant.new(merchant_params.merge(family: Current.family))
+
+    if @merchant.save
+      respond_to do |format|
+        format.html { redirect_to family_merchants_path, notice: t(".success") }
+        format.turbo_stream { render turbo_stream: turbo_stream.action(:redirect, family_merchants_path) }
+      end
+    else
+      render :new, status: :unprocessable_entity
+    end
+  end
+
+  def edit
+  end
+
+  def update
+    @merchant.update!(merchant_params)
+    respond_to do |format|
+      format.html { redirect_to family_merchants_path, notice: t(".success") }
+      format.turbo_stream { render turbo_stream: turbo_stream.action(:redirect, family_merchants_path) }
+    end
+  end
+
+  def destroy
+    @merchant.destroy!
+    redirect_to family_merchants_path, notice: t(".success")
+  end
+
+  private
+
+    def set_merchant
+      @merchant = Current.family.merchants.find(params[:id])
+    end
+
+    def merchant_params
+      params.require(:family_merchant).permit(:name, :color)
+    end
+end
diff --git a/app/controllers/merchants_controller.rb b/app/controllers/merchants_controller.rb
deleted file mode 100644
index cbcf1cdb..00000000
--- a/app/controllers/merchants_controller.rb
+++ /dev/null
@@ -1,46 +0,0 @@
-class MerchantsController < ApplicationController
-  before_action :set_merchant, only: %i[edit update destroy]
-
-  def index
-    @merchants = Current.family.merchants.alphabetically
-
-    render layout: "settings"
-  end
-
-  def new
-    @merchant = Merchant.new
-  end
-
-  def create
-    @merchant = Current.family.merchants.new(merchant_params)
-
-    if @merchant.save
-      redirect_to merchants_path, notice: t(".success")
-    else
-      redirect_to merchants_path, alert: t(".error", error: @merchant.errors.full_messages.to_sentence)
-    end
-  end
-
-  def edit
-  end
-
-  def update
-    @merchant.update!(merchant_params)
-    redirect_to merchants_path, notice: t(".success")
-  end
-
-  def destroy
-    @merchant.destroy!
-    redirect_to merchants_path, notice: t(".success")
-  end
-
-  private
-
-    def set_merchant
-      @merchant = Current.family.merchants.find(params[:id])
-    end
-
-    def merchant_params
-      params.require(:merchant).permit(:name, :color)
-    end
-end
diff --git a/app/controllers/rules_controller.rb b/app/controllers/rules_controller.rb
new file mode 100644
index 00000000..318ed60d
--- /dev/null
+++ b/app/controllers/rules_controller.rb
@@ -0,0 +1,77 @@
+class RulesController < ApplicationController
+  include StreamExtensions
+
+  before_action :set_rule, only: [  :edit, :update, :destroy, :apply, :confirm ]
+
+  def index
+    @rules = Current.family.rules.order(created_at: :desc)
+    render layout: "settings"
+  end
+
+  def new
+    @rule = Current.family.rules.build(
+      resource_type: params[:resource_type] || "transaction",
+    )
+  end
+
+  def create
+    @rule = Current.family.rules.build(rule_params)
+
+    if @rule.save
+      redirect_to confirm_rule_path(@rule)
+    else
+      render :new, status: :unprocessable_entity
+    end
+  end
+
+  def apply
+    @rule.update!(active: true)
+    @rule.apply_later(ignore_attribute_locks: true)
+    redirect_back_or_to rules_path, notice: "#{@rule.resource_type.humanize} rule activated"
+  end
+
+  def confirm
+  end
+
+  def edit
+  end
+
+  def update
+    if @rule.update(rule_params)
+      respond_to do |format|
+        format.html { redirect_back_or_to rules_path, notice: "Rule updated" }
+        format.turbo_stream { stream_redirect_back_or_to rules_path, notice: "Rule updated" }
+      end
+    else
+      render :edit, status: :unprocessable_entity
+    end
+  end
+
+  def destroy
+    @rule.destroy
+    redirect_to rules_path, notice: "Rule deleted"
+  end
+
+  def destroy_all
+    Current.family.rules.destroy_all
+    redirect_to rules_path, notice: "All rules deleted"
+  end
+
+  private
+    def set_rule
+      @rule = Current.family.rules.find(params[:id])
+    end
+
+    def rule_params
+      params.require(:rule).permit(
+        :resource_type, :effective_date, :active,
+        conditions_attributes: [
+          :id, :condition_type, :operator, :value, :_destroy,
+          sub_conditions_attributes: [ :id, :condition_type, :operator, :value, :_destroy ]
+        ],
+        actions_attributes: [
+          :id, :action_type, :value, :_destroy
+        ]
+      )
+    end
+end
diff --git a/app/controllers/trades_controller.rb b/app/controllers/trades_controller.rb
index 151d62c6..bd49459e 100644
--- a/app/controllers/trades_controller.rb
+++ b/app/controllers/trades_controller.rb
@@ -48,7 +48,7 @@ class TradesController < ApplicationController
 
     def entry_params
       params.require(:entry).permit(
-        :name, :enriched_name, :date, :amount, :currency, :excluded, :notes, :nature,
+        :name, :date, :amount, :currency, :excluded, :notes, :nature,
         entryable_attributes: [ :id, :qty, :price ]
       )
     end
diff --git a/app/controllers/transaction_categories_controller.rb b/app/controllers/transaction_categories_controller.rb
index f70e0aa9..dac6b5be 100644
--- a/app/controllers/transaction_categories_controller.rb
+++ b/app/controllers/transaction_categories_controller.rb
@@ -1,16 +1,34 @@
 class TransactionCategoriesController < ApplicationController
+  include ActionView::RecordIdentifier
+
   def update
     @entry = Current.family.entries.transactions.find(params[:transaction_id])
     @entry.update!(entry_params)
 
+    transaction = @entry.transaction
+
+    if needs_rule_notification?(transaction)
+      flash[:cta] = {
+        type: "category_rule",
+        category_id: transaction.category_id,
+        category_name: transaction.category.name
+      }
+    end
+
+    transaction.lock_saved_attributes!
+    @entry.lock_saved_attributes!
+
     respond_to do |format|
       format.html { redirect_back_or_to transaction_path(@entry) }
       format.turbo_stream do
-        render turbo_stream: turbo_stream.replace(
-          "category_menu_transaction_#{@entry.transaction_id}",
-          partial: "categories/menu",
-          locals: { transaction: @entry.transaction }
-        )
+        render turbo_stream: [
+          turbo_stream.replace(
+            dom_id(transaction, :category_menu),
+            partial: "categories/menu",
+            locals: { transaction: transaction }
+          ),
+          *flash_notification_stream_items
+        ]
       end
     end
   end
@@ -19,4 +37,16 @@ class TransactionCategoriesController < ApplicationController
     def entry_params
       params.require(:entry).permit(:entryable_type, entryable_attributes: [ :id, :category_id ])
     end
+
+    def needs_rule_notification?(transaction)
+      return false if Current.user.rule_prompts_disabled
+
+      if Current.user.rule_prompt_dismissed_at.present?
+        time_since_last_rule_prompt = Time.current - Current.user.rule_prompt_dismissed_at
+        return false if time_since_last_rule_prompt < 1.day
+      end
+
+      transaction.saved_change_to_category_id? &&
+      transaction.eligible_for_category_rule?
+    end
 end
diff --git a/app/controllers/transactions_controller.rb b/app/controllers/transactions_controller.rb
index e4407ee3..77044542 100644
--- a/app/controllers/transactions_controller.rb
+++ b/app/controllers/transactions_controller.rb
@@ -54,6 +54,8 @@ class TransactionsController < ApplicationController
 
     if @entry.save
       @entry.sync_account_later
+      @entry.lock_saved_attributes!
+      @entry.transaction.lock!(:tag_ids) if @entry.transaction.tags.any?
 
       flash[:notice] = "Transaction created"
 
@@ -68,7 +70,19 @@ class TransactionsController < ApplicationController
 
   def update
     if @entry.update(entry_params)
+      transaction = @entry.transaction
+
+      if needs_rule_notification?(transaction)
+        flash[:cta] = {
+          type: "category_rule",
+          category_id: transaction.category_id,
+          category_name: transaction.category.name
+        }
+      end
+
       @entry.sync_account_later
+      @entry.lock_saved_attributes!
+      @entry.transaction.lock!(:tag_ids) if @entry.transaction.tags.any?
 
       respond_to do |format|
         format.html { redirect_back_or_to account_path(@entry.account), notice: "Transaction updated" }
@@ -79,7 +93,8 @@ class TransactionsController < ApplicationController
               partial: "transactions/header",
               locals: { entry: @entry }
             ),
-            turbo_stream.replace(@entry)
+            turbo_stream.replace(@entry),
+            *flash_notification_stream_items
           ]
         end
       end
@@ -89,9 +104,21 @@ class TransactionsController < ApplicationController
   end
 
   private
+    def needs_rule_notification?(transaction)
+      return false if Current.user.rule_prompts_disabled
+
+      if Current.user.rule_prompt_dismissed_at.present?
+        time_since_last_rule_prompt = Time.current - Current.user.rule_prompt_dismissed_at
+        return false if time_since_last_rule_prompt < 1.day
+      end
+
+      transaction.saved_change_to_category_id? &&
+      transaction.eligible_for_category_rule?
+    end
+
     def entry_params
       entry_params = params.require(:entry).permit(
-        :name, :enriched_name, :date, :amount, :currency, :excluded, :notes, :nature, :entryable_type,
+        :name, :date, :amount, :currency, :excluded, :notes, :nature, :entryable_type,
         entryable_attributes: [ :id, :category_id, :merchant_id, { tag_ids: [] } ]
       )
 
diff --git a/app/controllers/users_controller.rb b/app/controllers/users_controller.rb
index 6cfefaec..0bf735f1 100644
--- a/app/controllers/users_controller.rb
+++ b/app/controllers/users_controller.rb
@@ -49,6 +49,11 @@ class UsersController < ApplicationController
     end
   end
 
+  def rule_prompt_settings
+    @user.update!(rule_prompt_settings_params)
+    redirect_back_or_to settings_profile_path
+  end
+
   private
     def handle_redirect(notice)
       case user_params[:redirect_to]
@@ -72,10 +77,14 @@ class UsersController < ApplicationController
       user_params[:email].present? && user_params[:email] != @user.email
     end
 
+    def rule_prompt_settings_params
+      params.require(:user).permit(:rule_prompt_dismissed_at, :rule_prompts_disabled)
+    end
+
     def user_params
       params.require(:user).permit(
         :first_name, :last_name, :email, :profile_image, :redirect_to, :delete_profile_image, :onboarded_at, :show_sidebar, :default_period, :show_ai_sidebar, :ai_enabled, :theme,
-        family_attributes: [ :name, :currency, :country, :locale, :date_format, :timezone, :id, :data_enrichment_enabled ]
+        family_attributes: [ :name, :currency, :country, :locale, :date_format, :timezone, :id ]
       )
     end
 
diff --git a/app/controllers/valuations_controller.rb b/app/controllers/valuations_controller.rb
index 7d91a9a6..a33e5457 100644
--- a/app/controllers/valuations_controller.rb
+++ b/app/controllers/valuations_controller.rb
@@ -44,6 +44,6 @@ class ValuationsController < ApplicationController
   private
     def entry_params
       params.require(:entry)
-            .permit(:name, :enriched_name, :date, :amount, :currency, :notes)
+            .permit(:name, :date, :amount, :currency, :notes)
     end
 end
diff --git a/app/helpers/application_helper.rb b/app/helpers/application_helper.rb
index 64321595..316e7900 100644
--- a/app/helpers/application_helper.rb
+++ b/app/helpers/application_helper.rb
@@ -27,24 +27,10 @@ module ApplicationHelper
     content_for(:header_description) { page_description }
   end
 
-  def family_notifications_stream
-    turbo_stream_from [ Current.family, :notifications ] if Current.family
-  end
-
   def family_stream
     turbo_stream_from Current.family if Current.family
   end
 
-  def render_flash_notifications
-    notifications = flash.flat_map do |type, message_or_messages|
-      Array(message_or_messages).map do |message|
-        render partial: "shared/notification", locals: { type: type, message: message }
-      end
-    end
-
-    safe_join(notifications)
-  end
-
   ##
   # Helper to open a centered and overlayed modal with custom contents
   #
@@ -53,9 +39,9 @@ module ApplicationHelper
   #     <div>Content here</div>
   #   <% end %>
   #
-  def modal(options = {}, &block)
+  def modal(reload_on_close: false, overflow_visible: false, &block)
     content = capture &block
-    render partial: "shared/modal", locals: { content:, classes: options[:classes] }
+    render partial: "shared/modal", locals: { content:, reload_on_close:, overflow_visible: }
   end
 
   ##
diff --git a/app/helpers/entries_helper.rb b/app/helpers/entries_helper.rb
index e198e6ee..1c3340ae 100644
--- a/app/helpers/entries_helper.rb
+++ b/app/helpers/entries_helper.rb
@@ -34,7 +34,7 @@ module EntriesHelper
       entry.date,
       format_money(entry.amount_money),
       entry.account.name,
-      entry.display_name
+      entry.name
     ].join(" • ")
   end
 end
diff --git a/app/helpers/forms_helper.rb b/app/helpers/forms_helper.rb
index 5e311810..53336757 100644
--- a/app/helpers/forms_helper.rb
+++ b/app/helpers/forms_helper.rb
@@ -4,10 +4,10 @@ module FormsHelper
     form_with(**options, &block)
   end
 
-  def modal_form_wrapper(title:, subtitle: nil, &block)
+  def modal_form_wrapper(title:, subtitle: nil, overflow_visible: false, &block)
     content = capture &block
 
-    render partial: "shared/modal_form", locals: { title:, subtitle:, content: }
+    render partial: "shared/modal_form", locals: { title:, subtitle:, content:, overflow_visible: }
   end
 
   def radio_tab_tag(form:, name:, value:, label:, icon:, checked: false, disabled: false, class: nil)
diff --git a/app/helpers/settings_helper.rb b/app/helpers/settings_helper.rb
index 674bea8b..dfe200c9 100644
--- a/app/helpers/settings_helper.rb
+++ b/app/helpers/settings_helper.rb
@@ -9,7 +9,8 @@ module SettingsHelper
     { name: I18n.t("settings.settings_nav.imports_label"), path: :imports_path },
     { name: I18n.t("settings.settings_nav.tags_label"), path: :tags_path },
     { name: I18n.t("settings.settings_nav.categories_label"), path: :categories_path },
-    { name: I18n.t("settings.settings_nav.merchants_label"), path: :merchants_path },
+    { name: "Rules", path: :rules_path },
+    { name: I18n.t("settings.settings_nav.merchants_label"), path: :family_merchants_path },
     { name: I18n.t("settings.settings_nav.whats_new_label"), path: :changelog_path },
     { name: I18n.t("settings.settings_nav.feedback_label"), path: :feedback_path }
   ]
diff --git a/app/javascript/controllers/modal_controller.js b/app/javascript/controllers/modal_controller.js
index 8c9d6c50..242c0247 100644
--- a/app/javascript/controllers/modal_controller.js
+++ b/app/javascript/controllers/modal_controller.js
@@ -22,7 +22,7 @@ export default class extends Controller {
     this.element.close();
 
     if (this.reloadOnCloseValue) {
-      window.location.reload();
+      Turbo.visit(window.location.href);
     }
   }
 }
diff --git a/app/javascript/controllers/rule/actions_controller.js b/app/javascript/controllers/rule/actions_controller.js
new file mode 100644
index 00000000..815e027e
--- /dev/null
+++ b/app/javascript/controllers/rule/actions_controller.js
@@ -0,0 +1,55 @@
+import { Controller } from "@hotwired/stimulus";
+
+// Connects to data-controller="rule--actions"
+export default class extends Controller {
+  static values = { actionExecutors: Array };
+  static targets = ["destroyField", "actionValue"];
+
+  remove(e) {
+    if (e.params.destroy) {
+      this.destroyFieldTarget.value = true;
+    } else {
+      this.element.remove();
+    }
+  }
+
+  handleActionTypeChange(e) {
+    const actionExecutor = this.actionExecutorsValue.find(
+      (executor) => executor.key === e.target.value,
+    );
+
+    if (actionExecutor.type === "select") {
+      this.#updateValueSelectFor(actionExecutor);
+      this.#showAndEnableValueSelect();
+    } else {
+      this.#hideAndDisableValueSelect();
+    }
+  }
+
+  get valueSelectEl() {
+    return this.actionValueTarget.querySelector("select");
+  }
+
+  #showAndEnableValueSelect() {
+    this.actionValueTarget.classList.remove("hidden");
+    this.valueSelectEl.disabled = false;
+  }
+
+  #hideAndDisableValueSelect() {
+    this.actionValueTarget.classList.add("hidden");
+    this.valueSelectEl.disabled = true;
+  }
+
+  #updateValueSelectFor(actionExecutor) {
+    // Clear existing options
+    this.valueSelectEl.innerHTML = "";
+
+    // Add new options
+    for (const option of actionExecutor.options) {
+      const optionEl = document.createElement("option");
+      optionEl.value = option[1];
+      optionEl.textContent = option[0];
+      this.valueSelectEl.appendChild(optionEl);
+    }
+  }
+}
diff --git a/app/javascript/controllers/rule/conditions_controller.js b/app/javascript/controllers/rule/conditions_controller.js
new file mode 100644
index 00000000..1cffa119
--- /dev/null
+++ b/app/javascript/controllers/rule/conditions_controller.js
@@ -0,0 +1,104 @@
+import { Controller } from "@hotwired/stimulus";
+
+// Connects to data-controller="rule--conditions"
+export default class extends Controller {
+  static values = { conditionFilters: Array };
+  static targets = [
+    "destroyField",
+    "filterValue",
+    "operatorSelect",
+    "subConditionTemplate",
+    "subConditionsList",
+  ];
+
+  addSubCondition() {
+    const html = this.subConditionTemplateTarget.innerHTML.replaceAll(
+      "IDX_PLACEHOLDER",
+      this.#uniqueKey(),
+    );
+
+    this.subConditionsListTarget.insertAdjacentHTML("beforeend", html);
+  }
+
+  remove(e) {
+    if (e.params.destroy) {
+      this.destroyFieldTarget.value = true;
+      this.element.classList.add("hidden");
+    } else {
+      this.element.remove();
+    }
+  }
+
+  handleConditionTypeChange(e) {
+    const conditionFilter = this.conditionFiltersValue.find(
+      (filter) => filter.key === e.target.value,
+    );
+
+    if (conditionFilter.type === "select") {
+      this.#buildSelectFor(conditionFilter);
+    } else {
+      this.#buildTextInputFor(conditionFilter);
+    }
+
+    this.#updateOperatorsField(conditionFilter);
+  }
+
+  get valueInputEl() {
+    const textInput = this.filterValueTarget.querySelector("input");
+    const selectInput = this.filterValueTarget.querySelector("select");
+
+    return textInput || selectInput;
+  }
+
+  #updateOperatorsField(conditionFilter) {
+    this.operatorSelectTarget.innerHTML = "";
+
+    for (const operator of conditionFilter.operators) {
+      const optionEl = document.createElement("option");
+      optionEl.value = operator[1];
+      optionEl.textContent = operator[0];
+      this.operatorSelectTarget.appendChild(optionEl);
+    }
+  }
+
+  #buildSelectFor(conditionFilter) {
+    const selectEl = this.#convertFormFieldTo("select", this.valueInputEl);
+
+    for (const option of conditionFilter.options) {
+      const optionEl = document.createElement("option");
+      optionEl.value = option[1];
+      optionEl.textContent = option[0];
+      selectEl.appendChild(optionEl);
+    }
+
+    this.valueInputEl.replaceWith(selectEl);
+  }
+
+  #buildTextInputFor(conditionFilter) {
+    const textInput = this.#convertFormFieldTo("input", this.valueInputEl);
+    textInput.placeholder = "Enter a value";
+    textInput.type = conditionFilter.type; // "text" || "number"
+    if (conditionFilter.type === "number") {
+      textInput.step = conditionFilter.number_step;
+    }
+
+    this.valueInputEl.replaceWith(textInput);
+  }
+
+  #convertFormFieldTo(type, el) {
+    const priorClasses = el.classList;
+    const priorId = el.id;
+    const priorName = el.name;
+
+    const newFormField = document.createElement(type);
+    newFormField.classList.add(...priorClasses);
+    newFormField.id = priorId;
+    newFormField.name = priorName;
+
+    return newFormField;
+  }
+
+  #uniqueKey() {
+    return Math.random().toString(36).substring(2, 15);
+  }
+}
diff --git a/app/javascript/controllers/rules_controller.js b/app/javascript/controllers/rules_controller.js
new file mode 100644
index 00000000..0db0e67a
--- /dev/null
+++ b/app/javascript/controllers/rules_controller.js
@@ -0,0 +1,48 @@
+import { Controller } from "@hotwired/stimulus";
+
+// Connects to data-controller="rules"
+export default class extends Controller {
+  static targets = [
+    "conditionTemplate",
+    "conditionGroupTemplate",
+    "actionTemplate",
+    "conditionsList",
+    "actionsList",
+    "effectiveDateInput",
+  ];
+
+  addConditionGroup() {
+    this.#appendTemplate(
+      this.conditionGroupTemplateTarget,
+      this.conditionsListTarget,
+    );
+  }
+
+  addCondition() {
+    this.#appendTemplate(
+      this.conditionTemplateTarget,
+      this.conditionsListTarget,
+    );
+  }
+
+  addAction() {
+    this.#appendTemplate(this.actionTemplateTarget, this.actionsListTarget);
+  }
+
+  clearEffectiveDate() {
+    this.effectiveDateInputTarget.value = "";
+  }
+
+  #appendTemplate(templateEl, listEl) {
+    const html = templateEl.innerHTML.replaceAll(
+      "IDX_PLACEHOLDER",
+      this.#uniqueKey(),
+    );
+
+    listEl.insertAdjacentHTML("beforeend", html);
+  }
+
+  #uniqueKey() {
+    return Date.now();
+  }
+}
diff --git a/app/jobs/auto_categorize_job.rb b/app/jobs/auto_categorize_job.rb
new file mode 100644
index 00000000..c31917a8
--- /dev/null
+++ b/app/jobs/auto_categorize_job.rb
@@ -0,0 +1,7 @@
+class AutoCategorizeJob < ApplicationJob
+  queue_as :medium_priority
+
+  def perform(family, transaction_ids: [])
+    family.auto_categorize_transactions(transaction_ids)
+  end
+end
diff --git a/app/jobs/auto_detect_merchants_job.rb b/app/jobs/auto_detect_merchants_job.rb
new file mode 100644
index 00000000..eb3713a4
--- /dev/null
+++ b/app/jobs/auto_detect_merchants_job.rb
@@ -0,0 +1,7 @@
+class AutoDetectMerchantsJob < ApplicationJob
+  queue_as :medium_priority
+
+  def perform(family, transaction_ids: [])
+    family.auto_detect_transaction_merchants(transaction_ids)
+  end
+end
diff --git a/app/jobs/enrich_transaction_batch_job.rb b/app/jobs/enrich_transaction_batch_job.rb
deleted file mode 100644
index 71aac720..00000000
--- a/app/jobs/enrich_transaction_batch_job.rb
+++ /dev/null
@@ -1,7 +0,0 @@
-class EnrichTransactionBatchJob < ApplicationJob
-  queue_as :low_priority
-
-  def perform(account, batch_size = 100, offset = 0)
-    account.enrich_transaction_batch(batch_size, offset)
-  end
-end
diff --git a/app/jobs/rule_job.rb b/app/jobs/rule_job.rb
new file mode 100644
index 00000000..fe446d0e
--- /dev/null
+++ b/app/jobs/rule_job.rb
@@ -0,0 +1,7 @@
+class RuleJob < ApplicationJob
+  queue_as :medium_priority
+
+  def perform(rule, ignore_attribute_locks: false)
+    rule.apply(ignore_attribute_locks: ignore_attribute_locks)
+  end
+end
diff --git a/app/models/account.rb b/app/models/account.rb
index 970c6ee5..6317fb94 100644
--- a/app/models/account.rb
+++ b/app/models/account.rb
@@ -1,5 +1,5 @@
 class Account < ApplicationRecord
-  include Syncable, Monetizable, Chartable, Enrichable, Linkable, Convertible
+  include Syncable, Monetizable, Chartable, Linkable, Convertible, Enrichable
 
   validates :name, :balance, :currency, presence: true
 
@@ -83,11 +83,6 @@ class Account < ApplicationRecord
 
     accountable.post_sync(sync)
 
-    if enrichable?
-      Rails.logger.info("Enriching transaction data")
-      enrich_data
-    end
-
     unless sync.child?
       family.auto_match_transfers!
     end
@@ -147,6 +142,11 @@ class Account < ApplicationRecord
     first_entry_date - 1.day
   end
 
+  def lock_saved_attributes!
+    super
+    accountable.lock_saved_attributes!
+  end
+
   def first_valuation
     entries.valuations.order(:date).first
   end
diff --git a/app/models/account/enrichable.rb b/app/models/account/enrichable.rb
deleted file mode 100644
index f5f175b4..00000000
--- a/app/models/account/enrichable.rb
+++ /dev/null
@@ -1,71 +0,0 @@
-module Account::Enrichable
-  extend ActiveSupport::Concern
-
-  def enrich_data
-    total_unenriched = entries.transactions
-      .joins("JOIN transactions at ON at.id = entries.entryable_id AND entries.entryable_type = 'Transaction'")
-      .where("entries.enriched_at IS NULL OR at.merchant_id IS NULL OR at.category_id IS NULL")
-      .count
-
-    if total_unenriched > 0
-      batch_size = 50
-      batches = (total_unenriched.to_f / batch_size).ceil
-
-      batches.times do |batch|
-        EnrichTransactionBatchJob.perform_now(self, batch_size, batch * batch_size)
-        # EnrichTransactionBatchJob.perform_later(self, batch_size, batch * batch_size)
-      end
-    end
-  end
-
-  def enrich_transaction_batch(batch_size = 50, offset = 0)
-    transactions_batch = enrichable_transactions.offset(offset).limit(batch_size)
-
-    Rails.logger.info("Enriching batch of #{transactions_batch.count} transactions for account #{id} (offset: #{offset})")
-
-    merchants = {}
-
-    transactions_batch.each do |transaction|
-      begin
-        info = transaction.fetch_enrichment_info
-
-        next unless info.present?
-
-        if info.name.present?
-          merchant = merchants[info.name] ||= family.merchants.find_or_create_by(name: info.name)
-
-          if info.icon_url.present?
-            merchant.icon_url = info.icon_url
-          end
-        end
-
-        Account.transaction do
-          merchant.save! if merchant.present?
-          transaction.update!(merchant: merchant) if merchant.present? && transaction.merchant_id.nil?
-
-          transaction.entry.update!(
-            enriched_at: Time.current,
-            enriched_name: info.name,
-          )
-        end
-      rescue => e
-        Rails.logger.warn("Error enriching transaction #{transaction.id}: #{e.message}")
-      end
-    end
-  end
-
-  private
-    def enrichable?
-      family.data_enrichment_enabled? || (linked? && Rails.application.config.app_mode.hosted?)
-    end
-
-    def enrichable_transactions
-      transactions.active
-                  .includes(:merchant, :category)
-                  .where(
-                    "entries.enriched_at IS NULL",
-                    "OR merchant_id IS NULL",
-                    "OR category_id IS NULL"
-                  )
-    end
-end
diff --git a/app/models/category.rb b/app/models/category.rb
index 56fd3a63..3c63c45a 100644
--- a/app/models/category.rb
+++ b/app/models/category.rb
@@ -50,11 +50,11 @@ class Category < ApplicationRecord
       %w[bus circle-dollar-sign ambulance apple award baby battery lightbulb bed-single beer bluetooth book briefcase building credit-card camera utensils cooking-pot cookie dices drama dog drill drum dumbbell gamepad-2 graduation-cap house hand-helping ice-cream-cone phone piggy-bank pill pizza printer puzzle ribbon shopping-cart shield-plus ticket trees]
     end
 
-    def bootstrap_defaults
-      default_categories.each do |name, color, icon|
+    def bootstrap!
+      default_categories.each do |name, color, icon, classification|
         find_or_create_by!(name: name) do |category|
           category.color = color
-          category.classification = "income" if name == "Income"
+          category.classification = classification
           category.lucide_icon = icon
         end
       end
@@ -71,18 +71,20 @@ class Category < ApplicationRecord
     private
       def default_categories
         [
-          [ "Income", "#e99537", "circle-dollar-sign" ],
-          [ "Housing", "#6471eb", "house" ],
-          [ "Entertainment", "#df4e92", "drama" ],
-          [ "Food & Drink", "#eb5429", "utensils" ],
-          [ "Shopping", "#e99537", "shopping-cart" ],
-          [ "Healthcare", "#4da568", "pill" ],
-          [ "Insurance", "#6471eb", "piggy-bank" ],
-          [ "Utilities", "#db5a54", "lightbulb" ],
-          [ "Transportation", "#df4e92", "bus" ],
-          [ "Education", "#eb5429", "book" ],
-          [ "Gifts & Donations", "#61c9ea", "hand-helping" ],
-          [ "Subscriptions", "#805dee", "credit-card" ]
+          [ "Income", "#e99537", "circle-dollar-sign", "income" ],
+          [ "Loan Payments", "#6471eb", "credit-card", "expense" ],
+          [ "Fees", "#6471eb", "credit-card", "expense" ],
+          [ "Entertainment", "#df4e92", "drama", "expense" ],
+          [ "Food & Drink", "#eb5429", "utensils", "expense" ],
+          [ "Shopping", "#e99537", "shopping-cart", "expense" ],
+          [ "Home Improvement", "#6471eb", "house", "expense" ],
+          [ "Healthcare", "#4da568", "pill", "expense" ],
+          [ "Personal Care", "#4da568", "pill", "expense" ],
+          [ "Services", "#4da568", "briefcase", "expense" ],
+          [ "Gifts & Donations", "#61c9ea", "hand-helping", "expense" ],
+          [ "Transportation", "#df4e92", "bus", "expense" ],
+          [ "Travel", "#df4e92", "plane", "expense" ],
+          [ "Rent & Utilities", "#db5a54", "lightbulb", "expense" ]
         ]
       end
   end
diff --git a/app/models/concerns/accountable.rb b/app/models/concerns/accountable.rb
index 2d545ec9..beb3cf23 100644
--- a/app/models/concerns/accountable.rb
+++ b/app/models/concerns/accountable.rb
@@ -9,6 +9,8 @@ module Accountable
   end
 
   included do
+    include Enrichable
+
     has_one :account, as: :accountable, touch: true
   end
 
diff --git a/app/models/concerns/enrichable.rb b/app/models/concerns/enrichable.rb
new file mode 100644
index 00000000..e5804786
--- /dev/null
+++ b/app/models/concerns/enrichable.rb
@@ -0,0 +1,63 @@
+# Enrichable models can have 1+ of their fields enriched by various
+# external sources (i.e. Plaid) or internal sources (i.e. Rules)
+#
+# This module defines how models should, lock, unlock, and edit attributes
+# based on the source of the edit.  User edits always take highest precedence.
+#
+# For example:
+#
+# If a Rule tells us to set the category to "Groceries", but the user later overrides
+# a transaction with a category of "Food", we should not override the category again.
+#
+module Enrichable
+  extend ActiveSupport::Concern
+
+  InvalidAttributeError = Class.new(StandardError)
+
+  included do
+    scope :enrichable, ->(attrs) {
+      attrs = Array(attrs).map(&:to_s)
+      json_condition = attrs.each_with_object({}) { |attr, hash| hash[attr] = true }
+      where.not(Arel.sql("#{table_name}.locked_attributes ?| array[:keys]"), keys: attrs)
+    }
+  end
+
+  def log_enrichment!(attribute_name:, attribute_value:, source:, metadata: {})
+    de = DataEnrichment.find_or_create_by!(
+      enrichable: self,
+      attribute_name: attribute_name,
+      source: source,
+    )
+
+    de.value = attribute_value
+    de.metadata = metadata
+    de.save!
+  end
+
+  def locked?(attr)
+    locked_attributes[attr.to_s].present?
+  end
+
+  def enrichable?(attr)
+    !locked?(attr)
+  end
+
+  def lock!(attr)
+    update!(locked_attributes: locked_attributes.merge(attr.to_s => Time.current))
+  end
+
+  def unlock!(attr)
+    update!(locked_attributes: locked_attributes.except(attr.to_s))
+  end
+
+  def lock_saved_attributes!
+    saved_changes.keys.reject { |attr| ignored_enrichable_attributes.include?(attr) }.each do |attr|
+      lock!(attr)
+    end
+  end
+
+  private
+    def ignored_enrichable_attributes
+      %w[id updated_at created_at]
+    end
+end
diff --git a/app/models/data_enrichment.rb b/app/models/data_enrichment.rb
new file mode 100644
index 00000000..df6a0d67
--- /dev/null
+++ b/app/models/data_enrichment.rb
@@ -0,0 +1,5 @@
+class DataEnrichment < ApplicationRecord
+  belongs_to :enrichable, polymorphic: true
+
+  enum :source, { rule: "rule", plaid: "plaid", synth: "synth", ai: "ai" }
+end
diff --git a/app/models/demo/generator.rb b/app/models/demo/generator.rb
index 181b9806..db479b08 100644
--- a/app/models/demo/generator.rb
+++ b/app/models/demo/generator.rb
@@ -40,7 +40,7 @@ class Demo::Generator
         create_tags!(family)
         create_categories!(family)
         create_merchants!(family)
-
+        create_rules!(family)
         puts "tags, categories, merchants created for #{family_name}"
 
         create_credit_card_account!(family)
@@ -152,7 +152,7 @@ class Demo::Generator
       Security::Price.destroy_all
     end
 
-    def create_family_and_user!(family_name, user_email, data_enrichment_enabled: false, currency: "USD")
+    def create_family_and_user!(family_name, user_email, currency: "USD")
       base_uuid = "d99e3c6e-d513-4452-8f24-dc263f8528c0"
       id = Digest::UUID.uuid_v5(base_uuid, family_name)
 
@@ -161,7 +161,6 @@ class Demo::Generator
         name: family_name,
         currency: currency,
         stripe_subscription_status: "active",
-        data_enrichment_enabled: data_enrichment_enabled,
         locale: "en",
         country: "US",
         timezone: "America/New_York",
@@ -185,6 +184,20 @@ class Demo::Generator
         onboarded_at: Time.current
     end
 
+    def create_rules!(family)
+      family.rules.create!(
+        effective_date: 1.year.ago.to_date,
+        active: true,
+        resource_type: "transaction",
+        conditions: [
+          Rule::Condition.new(condition_type: "transaction_merchant", operator: "=", value: "Whole Foods")
+        ],
+        actions: [
+          Rule::Action.new(action_type: "set_transaction_category", value: "Groceries")
+        ]
+      )
+    end
+
     def create_tags!(family)
       [ "Trips", "Emergency Fund", "Demo Tag" ].each do |tag|
         family.tags.create!(name: tag)
@@ -192,7 +205,7 @@ class Demo::Generator
     end
 
     def create_categories!(family)
-      family.categories.bootstrap_defaults
+      family.categories.bootstrap!
 
       food = family.categories.find_by(name: "Food & Drink")
       family.categories.create!(name: "Restaurants", parent: food, color: COLORS.sample, lucide_icon: "utensils", classification: "expense")
@@ -206,7 +219,7 @@ class Demo::Generator
                    "Uber", "Netflix", "Spotify", "Delta Airlines", "Airbnb", "Sephora" ]
 
       merchants.each do |merchant|
-        family.merchants.create!(name: merchant, color: COLORS.sample)
+        FamilyMerchant.create!(name: merchant, family: family, color: COLORS.sample)
       end
     end
 
diff --git a/app/models/entry.rb b/app/models/entry.rb
index 0f35cd39..c07f27cf 100644
--- a/app/models/entry.rb
+++ b/app/models/entry.rb
@@ -1,5 +1,5 @@
 class Entry < ApplicationRecord
-  include Monetizable
+  include Monetizable, Enrichable
 
   monetize :amount
 
@@ -34,6 +34,15 @@ class Entry < ApplicationRecord
     )
   }
 
+  def classification
+    amount.negative? ? "income" : "expense"
+  end
+
+  def lock_saved_attributes!
+    super
+    entryable.lock_saved_attributes!
+  end
+
   def sync_account_later
     sync_start_date = [ date_previously_was, date ].compact.min unless destroyed?
     account.sync_later(start_date: sync_start_date)
@@ -47,10 +56,6 @@ class Entry < ApplicationRecord
     Balance::TrendCalculator.new(self, entries, balances).trend
   end
 
-  def display_name
-    enriched_name.presence || name
-  end
-
   class << self
     def search(params)
       EntrySearch.new(params).build_query(all)
@@ -78,6 +83,9 @@ class Entry < ApplicationRecord
         all.each do |entry|
           bulk_attributes[:entryable_attributes][:id] = entry.entryable_id if bulk_attributes[:entryable_attributes].present?
           entry.update! bulk_attributes
+
+          entry.lock_saved_attributes!
+          entry.entryable.lock!(:tag_ids) if entry.transaction? && entry.transaction.tags.any?
         end
       end
 
diff --git a/app/models/entry_search.rb b/app/models/entry_search.rb
index bed87613..07793df4 100644
--- a/app/models/entry_search.rb
+++ b/app/models/entry_search.rb
@@ -16,7 +16,7 @@ class EntrySearch
       return scope if search.blank?
 
       query = scope
-      query = query.where("entries.name ILIKE :search OR entries.enriched_name ILIKE :search",
+      query = query.where("entries.name ILIKE :search",
         search: "%#{ActiveRecord::Base.sanitize_sql_like(search)}%"
       )
       query
diff --git a/app/models/entryable.rb b/app/models/entryable.rb
index 84ab6c12..2c93786c 100644
--- a/app/models/entryable.rb
+++ b/app/models/entryable.rb
@@ -8,6 +8,8 @@ module Entryable
   end
 
   included do
+    include Enrichable
+
     has_one :entry, as: :entryable, touch: true
 
     scope :with_entry, -> { joins(:entry) }
diff --git a/app/models/family.rb b/app/models/family.rb
index 413c969b..caaa4134 100644
--- a/app/models/family.rb
+++ b/app/models/family.rb
@@ -22,12 +22,13 @@ class Family < ApplicationRecord
 
   has_many :entries, through: :accounts
   has_many :transactions, through: :accounts
+  has_many :rules, dependent: :destroy
   has_many :trades, through: :accounts
   has_many :holdings, through: :accounts
 
   has_many :tags, dependent: :destroy
   has_many :categories, dependent: :destroy
-  has_many :merchants, dependent: :destroy
+  has_many :merchants, dependent: :destroy, class_name: "FamilyMerchant"
 
   has_many :budgets, dependent: :destroy
   has_many :budget_categories, through: :budgets
@@ -35,6 +36,27 @@ class Family < ApplicationRecord
   validates :locale, inclusion: { in: I18n.available_locales.map(&:to_s) }
   validates :date_format, inclusion: { in: DATE_FORMATS.map(&:last) }
 
+  def assigned_merchants
+    merchant_ids = transactions.where.not(merchant_id: nil).pluck(:merchant_id).uniq
+    Merchant.where(id: merchant_ids)
+  end
+
+  def auto_categorize_transactions_later(transactions)
+    AutoCategorizeJob.perform_later(self, transaction_ids: transactions.pluck(:id))
+  end
+
+  def auto_categorize_transactions(transaction_ids)
+    AutoCategorizer.new(self, transaction_ids: transaction_ids).auto_categorize
+  end
+
+  def auto_detect_transaction_merchants_later(transactions)
+    AutoDetectMerchantsJob.perform_later(self, transaction_ids: transactions.pluck(:id))
+  end
+
+  def auto_detect_transaction_merchants(transaction_ids)
+    AutoMerchantDetector.new(self, transaction_ids: transaction_ids).auto_detect
+  end
+
   def balance_sheet
     @balance_sheet ||= BalanceSheet.new(self)
   end
@@ -46,13 +68,20 @@ class Family < ApplicationRecord
   def sync_data(sync, start_date: nil)
     update!(last_synced_at: Time.current)
 
+    Rails.logger.info("Syncing accounts for family #{id}")
     accounts.manual.each do |account|
       account.sync_later(start_date: start_date, parent_sync: sync)
     end
 
+    Rails.logger.info("Syncing plaid items for family #{id}")
     plaid_items.each do |plaid_item|
       plaid_item.sync_later(start_date: start_date, parent_sync: sync)
     end
+
+    Rails.logger.info("Applying rules for family #{id}")
+    rules.each do |rule|
+      rule.apply_later
+    end
   end
 
   def remove_syncing_notice!
@@ -138,4 +167,8 @@ class Family < ApplicationRecord
       entries.maximum(:updated_at)
     ].compact.join("_")
   end
+
+  def self_hoster?
+    Rails.application.config.app_mode.self_hosted?
+  end
 end
diff --git a/app/models/family/auto_categorizer.rb b/app/models/family/auto_categorizer.rb
new file mode 100644
index 00000000..c35aa3b9
--- /dev/null
+++ b/app/models/family/auto_categorizer.rb
@@ -0,0 +1,88 @@
+class Family::AutoCategorizer
+  Error = Class.new(StandardError)
+
+  def initialize(family, transaction_ids: [])
+    @family = family
+    @transaction_ids = transaction_ids
+  end
+
+  def auto_categorize
+    raise Error, "No LLM provider for auto-categorization" unless llm_provider
+
+    if scope.none?
+      Rails.logger.info("No transactions to auto-categorize for family #{family.id}")
+      return
+    else
+      Rails.logger.info("Auto-categorizing #{scope.count} transactions for family #{family.id}")
+    end
+
+    result = llm_provider.auto_categorize(
+      transactions: transactions_input,
+      user_categories: user_categories_input
+    )
+
+    unless result.success?
+      Rails.logger.error("Failed to auto-categorize transactions for family #{family.id}: #{result.error.message}")
+      return
+    end
+
+    scope.each do |transaction|
+      transaction.lock!(:category_id)
+
+      auto_categorization = result.data.find { |c| c.transaction_id == transaction.id }
+
+      category_id = user_categories_input.find { |c| c[:name] == auto_categorization&.category_name }&.dig(:id)
+
+      if category_id.present?
+        Family.transaction do
+          transaction.log_enrichment!(
+            attribute_name: "category_id",
+            attribute_value: category_id,
+            source: "ai",
+          )
+
+          transaction.update!(category_id: category_id)
+        end
+      end
+    end
+  end
+
+  private
+    attr_reader :family, :transaction_ids
+
+    # For now, OpenAI only, but this should work with any LLM concept provider
+    def llm_provider
+      Provider::Registry.get_provider(:openai)
+    end
+
+    def user_categories_input
+      family.categories.map do |category|
+        {
+          id: category.id,
+          name: category.name,
+          is_subcategory: category.subcategory?,
+          parent_id: category.parent_id,
+          classification: category.classification
+        }
+      end
+    end
+
+    def transactions_input
+      scope.map do |transaction|
+        {
+          id: transaction.id,
+          amount: transaction.entry.amount.abs,
+          classification: transaction.entry.classification,
+          description: transaction.entry.name,
+          merchant: transaction.merchant&.name,
+          hint: transaction.plaid_category_detailed
+        }
+      end
+    end
+
+    def scope
+      family.transactions.where(id: transaction_ids, category_id: nil)
+                         .enrichable(:category_id)
+                         .includes(:category, :merchant, :entry)
+    end
+end
diff --git a/app/models/family/auto_merchant_detector.rb b/app/models/family/auto_merchant_detector.rb
new file mode 100644
index 00000000..4b791e7a
--- /dev/null
+++ b/app/models/family/auto_merchant_detector.rb
@@ -0,0 +1,100 @@
+class Family::AutoMerchantDetector
+  Error = Class.new(StandardError)
+
+  def initialize(family, transaction_ids: [])
+    @family = family
+    @transaction_ids = transaction_ids
+  end
+
+  def auto_detect
+    raise "No LLM provider for auto-detecting merchants" unless llm_provider
+
+    if scope.none?
+      Rails.logger.info("No transactions to auto-detect merchants for family #{family.id}")
+      return
+    else
+      Rails.logger.info("Auto-detecting merchants for #{scope.count} transactions for family #{family.id}")
+    end
+
+    result = llm_provider.auto_detect_merchants(
+      transactions: transactions_input,
+      user_merchants: user_merchants_input
+    )
+
+    unless result.success?
+      Rails.logger.error("Failed to auto-detect merchants for family #{family.id}: #{result.error.message}")
+      return
+    end
+
+    scope.each do |transaction|
+      transaction.lock!(:merchant_id)
+
+      auto_detection = result.data.find { |c| c.transaction_id == transaction.id }
+
+      merchant_id = user_merchants_input.find { |m| m[:name] == auto_detection&.business_name }&.dig(:id)
+
+      if merchant_id.nil? && auto_detection&.business_url.present? && auto_detection&.business_name.present?
+        ai_provider_merchant = ProviderMerchant.find_or_create_by!(
+          source: "ai",
+          name: auto_detection.business_name,
+          website_url: auto_detection.business_url,
+        ) do |pm|
+          pm.logo_url = "#{default_logo_provider_url}/#{auto_detection.business_url}"
+        end
+      end
+
+      merchant_id = merchant_id || ai_provider_merchant&.id
+
+      if merchant_id.present?
+        Family.transaction do
+          transaction.log_enrichment!(
+            attribute_name: "merchant_id",
+            attribute_value: merchant_id,
+            source: "ai",
+          )
+
+          transaction.update!(merchant_id: merchant_id)
+        end
+      end
+    end
+  end
+
+  private
+    attr_reader :family, :transaction_ids
+
+    # For now, OpenAI only, but this should work with any LLM concept provider
+    def llm_provider
+      Provider::Registry.get_provider(:openai)
+    end
+
+    def default_logo_provider_url
+      "https://logo.synthfinance.com"
+    end
+
+    def user_merchants_input
+      family.merchants.map do |merchant|
+        {
+          id: merchant.id,
+          name: merchant.name
+        }
+      end
+    end
+
+    def transactions_input
+      scope.map do |transaction|
+        {
+          id: transaction.id,
+          amount: transaction.entry.amount.abs,
+          classification: transaction.entry.classification,
+          description: transaction.entry.name,
+          merchant: transaction.merchant&.name
+        }
+      end
+    end
+
+    def scope
+      family.transactions.where(id: transaction_ids, merchant_id: nil)
+                         .enrichable(:merchant_id)
+                         .includes(:merchant, :entry)
+    end
+end
diff --git a/app/models/family_merchant.rb b/app/models/family_merchant.rb
new file mode 100644
index 00000000..eeb88188
--- /dev/null
+++ b/app/models/family_merchant.rb
@@ -0,0 +1,15 @@
+class FamilyMerchant < Merchant
+  COLORS = %w[#e99537 #4da568 #6471eb #db5a54 #df4e92 #c44fe9 #eb5429 #61c9ea #805dee #6ad28a]
+
+  belongs_to :family
+
+  before_validation :set_default_color
+
+  validates :color, presence: true
+  validates :name, uniqueness: { scope: :family }
+
+  private
+    def set_default_color
+      self.color = COLORS.sample
+    end
+end
diff --git a/app/models/merchant.rb b/app/models/merchant.rb
index 030d9409..4a4257bc 100644
--- a/app/models/merchant.rb
+++ b/app/models/merchant.rb
@@ -1,11 +1,10 @@
 class Merchant < ApplicationRecord
-  has_many :transactions, dependent: :nullify, class_name: "Transaction"
-  belongs_to :family
+  TYPES = %w[FamilyMerchant ProviderMerchant].freeze
 
-  validates :name, :color, :family, presence: true
-  validates :name, uniqueness: { scope: :family }
+  has_many :transactions, dependent: :nullify
+
+  validates :name, presence: true
+  validates :type, inclusion: { in: TYPES }
 
   scope :alphabetically, -> { order(:name) }
-
-  COLORS = %w[#e99537 #4da568 #6471eb #db5a54 #df4e92 #c44fe9 #eb5429 #61c9ea #805dee #6ad28a]
 end
diff --git a/app/models/plaid_account.rb b/app/models/plaid_account.rb
index 4f2b923c..65acf9ae 100644
--- a/app/models/plaid_account.rb
+++ b/app/models/plaid_account.rb
@@ -83,13 +83,14 @@ class PlaidAccount < ApplicationRecord
   def sync_transactions!(added:, modified:, removed:)
     added.each do |plaid_txn|
       account.entries.find_or_create_by!(plaid_id: plaid_txn.transaction_id) do |t|
-        t.name = plaid_txn.name
+        t.name = plaid_txn.merchant_name || plaid_txn.original_description
         t.amount = plaid_txn.amount
         t.currency = plaid_txn.iso_currency_code
         t.date = plaid_txn.date
         t.entryable = Transaction.new(
-          category: get_category(plaid_txn.personal_finance_category.primary),
-          merchant: get_merchant(plaid_txn.merchant_name)
+          plaid_category: plaid_txn.personal_finance_category.primary,
+          plaid_category_detailed: plaid_txn.personal_finance_category.detailed,
+          merchant: find_or_create_merchant(plaid_txn)
         )
       end
     end
@@ -99,7 +100,12 @@ class PlaidAccount < ApplicationRecord
 
       existing_txn.update!(
         amount: plaid_txn.amount,
-        date: plaid_txn.date
+        date: plaid_txn.date,
+        entryable_attributes: {
+          plaid_category: plaid_txn.personal_finance_category.primary,
+          plaid_category_detailed: plaid_txn.personal_finance_category.detailed,
+          merchant: find_or_create_merchant(plaid_txn)
+        }
       )
     end
 
@@ -125,19 +131,19 @@ class PlaidAccount < ApplicationRecord
       end
     end
 
-    # See https://plaid.com/documents/transactions-personal-finance-category-taxonomy.csv
-    def get_category(plaid_category)
-      ignored_categories = [ "BANK_FEES", "TRANSFER_IN", "TRANSFER_OUT", "LOAN_PAYMENTS", "OTHER" ]
+    def find_or_create_merchant(plaid_txn)
+      unless plaid_txn.merchant_entity_id.present? && plaid_txn.merchant_name.present?
+        return nil
+      end
 
-      return nil if ignored_categories.include?(plaid_category)
-
-      family.categories.find_or_create_by!(name: plaid_category.titleize)
-    end
-
-    def get_merchant(plaid_merchant_name)
-      return nil if plaid_merchant_name.blank?
-
-      family.merchants.find_or_create_by!(name: plaid_merchant_name)
+      ProviderMerchant.find_or_create_by!(
+        source: "plaid",
+        name: plaid_txn.merchant_name,
+      ) do |m|
+        m.provider_merchant_id = plaid_txn.merchant_entity_id
+        m.website_url = plaid_txn.website
+        m.logo_url = plaid_txn.logo_url
+      end
     end
 
     def derive_plaid_cash_balance(plaid_balances)
diff --git a/app/models/plaid_item.rb b/app/models/plaid_item.rb
index 93a3a13e..baab5104 100644
--- a/app/models/plaid_item.rb
+++ b/app/models/plaid_item.rb
@@ -80,6 +80,7 @@ class PlaidItem < ApplicationRecord
   end
 
   def post_sync(sync)
+    auto_match_categories!
     family.broadcast_refresh
   end
 
@@ -88,6 +89,36 @@ class PlaidItem < ApplicationRecord
     DestroyJob.perform_later(self)
   end
 
+  def auto_match_categories!
+    if family.categories.none?
+      family.categories.bootstrap!
+    end
+
+    alias_matcher = build_category_alias_matcher(family.categories)
+
+    accounts.each do |account|
+      matchable_transactions = account.transactions
+                                      .where(category_id: nil)
+                                      .where.not(plaid_category: nil)
+                                      .enrichable(:category_id)
+
+      matchable_transactions.each do |transaction|
+        category = alias_matcher.match(transaction.plaid_category_detailed)
+
+        if category.present?
+          PlaidItem.transaction do
+            transaction.log_enrichment!(
+              attribute_name: "category_id",
+              attribute_value: category.id,
+              source: "plaid"
+            )
+            transaction.set_category!(category)
+          end
+        end
+      end
+    end
+  end
+
   private
     def fetch_and_load_plaid_data
       data = {}
diff --git a/app/models/plaid_item/provided.rb b/app/models/plaid_item/provided.rb
index 3d857e4b..f2e8ee8f 100644
--- a/app/models/plaid_item/provided.rb
+++ b/app/models/plaid_item/provided.rb
@@ -15,6 +15,10 @@ module PlaidItem::Provided
     end
   end
 
+  def build_category_alias_matcher(user_categories)
+    Provider::Plaid::CategoryAliasMatcher.new(user_categories)
+  end
+
   private
     def eu?
       raise "eu? is not implemented for #{self.class.name}"
diff --git a/app/models/provider/llm_concept.rb b/app/models/provider/llm_concept.rb
index dbdf1eb4..3459ab53 100644
--- a/app/models/provider/llm_concept.rb
+++ b/app/models/provider/llm_concept.rb
@@ -1,6 +1,18 @@
 module Provider::LlmConcept
   extend ActiveSupport::Concern
 
+  AutoCategorization = Data.define(:transaction_id, :category_name)
+
+  def auto_categorize(transactions)
+    raise NotImplementedError, "Subclasses must implement #auto_categorize"
+  end
+
+  AutoDetectedMerchant = Data.define(:transaction_id, :business_name, :business_url)
+
+  def auto_detect_merchants(transactions)
+    raise NotImplementedError, "Subclasses must implement #auto_detect_merchants"
+  end
+
   ChatMessage = Data.define(:id, :output_text)
   ChatStreamChunk = Data.define(:type, :data)
   ChatResponse = Data.define(:id, :model, :messages, :function_requests)
diff --git a/app/models/provider/openai.rb b/app/models/provider/openai.rb
index 70b42056..1268203a 100644
--- a/app/models/provider/openai.rb
+++ b/app/models/provider/openai.rb
@@ -14,6 +14,30 @@ class Provider::Openai < Provider
     MODELS.include?(model)
   end
 
+  def auto_categorize(transactions: [], user_categories: [])
+    with_provider_response do
+      raise Error, "Too many transactions to auto-categorize. Max is 25 per request." if transactions.size > 25
+
+      AutoCategorizer.new(
+        client,
+        transactions: transactions,
+        user_categories: user_categories
+      ).auto_categorize
+    end
+  end
+
+  def auto_detect_merchants(transactions: [], user_merchants: [])
+    with_provider_response do
+      raise Error, "Too many transactions to auto-detect merchants. Max is 25 per request." if transactions.size > 25
+
+      AutoMerchantDetector.new(
+        client,
+        transactions: transactions,
+        user_merchants: user_merchants
+      ).auto_detect_merchants
+    end
+  end
+
   def chat_response(prompt, model:, instructions: nil, functions: [], function_results: [], streamer: nil, previous_response_id: nil)
     with_provider_response do
       chat_config = ChatConfig.new(
diff --git a/app/models/provider/openai/auto_categorizer.rb b/app/models/provider/openai/auto_categorizer.rb
new file mode 100644
index 00000000..6d3e5e8a
--- /dev/null
+++ b/app/models/provider/openai/auto_categorizer.rb
@@ -0,0 +1,120 @@
+class Provider::Openai::AutoCategorizer
+  def initialize(client, transactions: [], user_categories: [])
+    @client = client
+    @transactions = transactions
+    @user_categories = user_categories
+  end
+
+  def auto_categorize
+    response = client.responses.create(parameters: {
+      model: "gpt-4.1-mini",
+      input: [ { role: "developer", content: developer_message } ],
+      text: {
+        format: {
+          type: "json_schema",
+          name: "auto_categorize_personal_finance_transactions",
+          strict: true,
+          schema: json_schema
+        }
+      },
+      instructions: instructions
+    })
+
+    Rails.logger.info("Tokens used to auto-categorize transactions: #{response.dig("usage").dig("total_tokens")}")
+
+    build_response(extract_categorizations(response))
+  end
+
+  private
+    attr_reader :client, :transactions, :user_categories
+
+    AutoCategorization = Provider::LlmConcept::AutoCategorization
+
+    def build_response(categorizations)
+      categorizations.map do |categorization|
+        AutoCategorization.new(
+          transaction_id: categorization.dig("transaction_id"),
+          category_name: normalize_category_name(categorization.dig("category_name")),
+        )
+      end
+    end
+
+    def normalize_category_name(category_name)
+      return nil if category_name == "null"
+
+      category_name
+    end
+
+    def extract_categorizations(response)
+      response_json = JSON.parse(response.dig("output")[0].dig("content")[0].dig("text"))
+      response_json.dig("categorizations")
+    end
+
+    def json_schema
+      {
+        type: "object",
+        properties: {
+          categorizations: {
+            type: "array",
+            description: "An array of auto-categorizations for each transaction",
+            items: {
+              type: "object",
+              properties: {
+                transaction_id: {
+                  type: "string",
+                  description: "The internal ID of the original transaction",
+                  enum: transactions.map { |t| t[:id] }
+                },
+                category_name: {
+                  type: "string",
+                  description: "The matched category name of the transaction, or null if no match",
+                  enum: [ *user_categories.map { |c| c[:name] }, "null" ]
+                }
+              },
+              required: [ "transaction_id", "category_name" ],
+              additionalProperties: false
+            }
+          }
+        },
+        required: [ "categorizations" ],
+        additionalProperties: false
+      }
+    end
+
+    def developer_message
+      <<~MESSAGE.strip_heredoc
+        Here are the user's available categories in JSON format:
+
+        ```json
+        #{user_categories.to_json}
+        ```
+
+        Use the available categories to auto-categorize the following transactions:
+
+        ```json
+        #{transactions.to_json}
+        ```
+      MESSAGE
+    end
+
+    def instructions
+      <<~INSTRUCTIONS.strip_heredoc
+        You are an assistant to a consumer personal finance app.  You will be provided a list
+        of the user's transactions and a list of the user's categories.  Your job is to auto-categorize
+        each transaction.
+
+        Closely follow ALL the rules below while auto-categorizing:
+
+        - Return 1 result per transaction
+        - Correlate each transaction by ID (transaction_id)
+        - Attempt to match the most specific category possible (i.e. subcategory over parent category)
+        - Category and transaction classifications should match (i.e. if transaction is an "expense", the category must have classification of "expense")
+        - If you don't know the category, return "null"
+          - You should always favor "null" over false positives
+          - Be slightly pessimistic.  Only match a category if you're 60%+ confident it is the correct one.
+        - Each transaction has varying metadata that can be used to determine the category
+          - Note: "hint" comes from 3rd party aggregators and typically represents a category name that
+            may or may not match any of the user-supplied categories
+      INSTRUCTIONS
+    end
+end
diff --git a/app/models/provider/openai/auto_merchant_detector.rb b/app/models/provider/openai/auto_merchant_detector.rb
new file mode 100644
index 00000000..f66ca2e7
--- /dev/null
+++ b/app/models/provider/openai/auto_merchant_detector.rb
@@ -0,0 +1,146 @@
+class Provider::Openai::AutoMerchantDetector
+  def initialize(client, transactions:, user_merchants:)
+    @client = client
+    @transactions = transactions
+    @user_merchants = user_merchants
+  end
+
+  def auto_detect_merchants
+    response = client.responses.create(parameters: {
+      model: "gpt-4.1-mini",
+      input: [ { role: "developer", content: developer_message } ],
+      text: {
+        format: {
+          type: "json_schema",
+          name: "auto_detect_personal_finance_merchants",
+          strict: true,
+          schema: json_schema
+        }
+      },
+      instructions: instructions
+    })
+
+    Rails.logger.info("Tokens used to auto-detect merchants: #{response.dig("usage").dig("total_tokens")}")
+
+    build_response(extract_categorizations(response))
+  end
+
+  private
+    attr_reader :client, :transactions, :user_merchants
+
+    AutoDetectedMerchant = Provider::LlmConcept::AutoDetectedMerchant
+
+    def build_response(categorizations)
+      categorizations.map do |categorization|
+        AutoDetectedMerchant.new(
+          transaction_id: categorization.dig("transaction_id"),
+          business_name: normalize_ai_value(categorization.dig("business_name")),
+          business_url: normalize_ai_value(categorization.dig("business_url")),
+        )
+      end
+    end
+
+    def normalize_ai_value(ai_value)
+      return nil if ai_value == "null"
+
+      ai_value
+    end
+
+    def extract_categorizations(response)
+      response_json = JSON.parse(response.dig("output")[0].dig("content")[0].dig("text"))
+      response_json.dig("merchants")
+    end
+
+    def json_schema
+      {
+        type: "object",
+        properties: {
+          merchants: {
+            type: "array",
+            description: "An array of auto-detected merchant businesses for each transaction",
+            items: {
+              type: "object",
+              properties: {
+                transaction_id: {
+                  type: "string",
+                  description: "The internal ID of the original transaction",
+                  enum: transactions.map { |t| t[:id] }
+                },
+                business_name: {
+                  type: [ "string", "null" ],
+                  description: "The detected business name of the transaction, or `null` if uncertain"
+                },
+                business_url: {
+                  type: [ "string", "null" ],
+                  description: "The URL of the detected business, or `null` if uncertain"
+                }
+              },
+              required: [ "transaction_id", "business_name", "business_url" ],
+              additionalProperties: false
+            }
+          }
+        },
+        required: [ "merchants" ],
+        additionalProperties: false
+      }
+    end
+
+    def developer_message
+      <<~MESSAGE.strip_heredoc
+        Here are the user's available merchants in JSON format:
+
+        ```json
+        #{user_merchants.to_json}
+        ```
+
+        Use BOTH your knowledge AND the user-generated merchants to auto-detect the following transactions:
+
+        ```json
+        #{transactions.to_json}
+        ```
+
+        Return "null" if you are not 80%+ confident in your answer.
+      MESSAGE
+    end
+
+    def instructions
+      <<~INSTRUCTIONS.strip_heredoc
+        You are an assistant to a consumer personal finance app.
+
+        Closely follow ALL the rules below while auto-detecting business names and website URLs:
+
+        - Return 1 result per transaction
+        - Correlate each transaction by ID (transaction_id)
+        - Do not include the subdomain in the business_url (i.e. "amazon.com" not "www.amazon.com")
+        - User merchants are considered "manual" user-generated merchants and should only be used in 100% clear cases
+        - Be slightly pessimistic.  We favor returning "null" over returning a false positive.
+        - NEVER return a name or URL for generic transaction names (e.g. "Paycheck", "Laundromat", "Grocery store", "Local diner")
+
+        Determining a value:
+
+        - First attempt to determine the name + URL from your knowledge of global businesses
+        - If no certain match, attempt to match one of the user-provided merchants
+        - If no match, return "null"
+
+        Example 1 (known business):
+
+        ```
+        Transaction name: "Some Amazon purchases"
+
+        Result:
+        - business_name: "Amazon"
+        - business_url: "amazon.com"
+        ```
+
+        Example 2 (generic business):
+
+        ```
+        Transaction name: "local diner"
+
+        Result:
+        - business_name: null
+        - business_url: null
+        ```
+      INSTRUCTIONS
+    end
+end
diff --git a/app/models/provider/plaid.rb b/app/models/provider/plaid.rb
index 8ac3b43d..ac5fe0f4 100644
--- a/app/models/provider/plaid.rb
+++ b/app/models/provider/plaid.rb
@@ -121,7 +121,10 @@ class Provider::Plaid
     while has_more
       request = Plaid::TransactionsSyncRequest.new(
         access_token: item.access_token,
-        cursor: cursor
+        cursor: cursor,
+        options: {
+          include_original_description: true
+        }
       )
 
       response = client.transactions_sync(request)
diff --git a/app/models/provider/plaid/category_alias_matcher.rb b/app/models/provider/plaid/category_alias_matcher.rb
new file mode 100644
index 00000000..41ada3a6
--- /dev/null
+++ b/app/models/provider/plaid/category_alias_matcher.rb
@@ -0,0 +1,109 @@
+# The purpose of this matcher is to auto-match Plaid categories to
+# known internal user categories.  Since we allow users to define their own
+# categories we cannot directly assign Plaid categories as this would overwrite
+# user data and create a confusing experience.
+#
+# Automated category matching in the Maybe app has a hierarchy:
+# 1. Naive string matching via CategoryAliasMatcher
+# 2. Rules-based matching set by user
+# 3. AI-powered matching (also enabled by user via rules)
+#
+# This class is simply a FAST and CHEAP way to match categories that are high confidence.
+# Edge cases will be handled by user-defined rules.
+class Provider::Plaid::CategoryAliasMatcher
+  include Provider::Plaid::CategoryTaxonomy
+
+  def initialize(user_categories)
+    @user_categories = user_categories
+  end
+
+  def match(plaid_detailed_category)
+    plaid_category_details = get_plaid_category_details(plaid_detailed_category)
+    return nil unless plaid_category_details
+
+    # Try exact name matches first
+    exact_match = normalized_user_categories.find do |category|
+      category[:name] == plaid_category_details[:key].to_s
+    end
+    return user_categories.find { |c| c.id == exact_match[:id] } if exact_match
+
+    # Try detailed aliases matches with fuzzy matching
+    alias_match = normalized_user_categories.find do |category|
+      name = category[:name]
+      plaid_category_details[:aliases].any? do |a|
+        alias_str = a.to_s
+
+        # Try exact match
+        next true if name == alias_str
+
+        # Try plural forms
+        next true if name.singularize == alias_str || name.pluralize == alias_str
+        next true if alias_str.singularize == name || alias_str.pluralize == name
+
+        # Try common forms
+        normalized_name = name.gsub(/(and|&|\s+)/, "").strip
+        normalized_alias = alias_str.gsub(/(and|&|\s+)/, "").strip
+        normalized_name == normalized_alias
+      end
+    end
+    return user_categories.find { |c| c.id == alias_match[:id] } if alias_match
+
+    # Try parent aliases matches with fuzzy matching
+    parent_match = normalized_user_categories.find do |category|
+      name = category[:name]
+      plaid_category_details[:parent_aliases].any? do |a|
+        alias_str = a.to_s
+
+        # Try exact match
+        next true if name == alias_str
+
+        # Try plural forms
+        next true if name.singularize == alias_str || name.pluralize == alias_str
+        next true if alias_str.singularize == name || alias_str.pluralize == name
+
+        # Try common forms
+        normalized_name = name.gsub(/(and|&|\s+)/, "").strip
+        normalized_alias = alias_str.gsub(/(and|&|\s+)/, "").strip
+        normalized_name == normalized_alias
+      end
+    end
+    return user_categories.find { |c| c.id == parent_match[:id] } if parent_match
+
+    nil
+  end
+
+  private
+    attr_reader :user_categories
+
+    def get_plaid_category_details(plaid_category_name)
+      detailed_plaid_categories.find { |c| c[:key] == plaid_category_name.downcase.to_sym }
+    end
+
+    def detailed_plaid_categories
+      CATEGORIES_MAP.flat_map do |parent_key, parent_data|
+        parent_data[:detailed_categories].map do |child_key, child_data|
+          {
+            key: child_key,
+            classification: child_data[:classification],
+            aliases: child_data[:aliases],
+            parent_key: parent_key,
+            parent_aliases: parent_data[:aliases]
+          }
+        end
+      end
+    end
+
+    def normalized_user_categories
+      user_categories.map do |user_category|
+        {
+          id: user_category.id,
+          classification: user_category.classification,
+          name: normalize_user_category_name(user_category.name)
+        }
+      end
+    end
+
+    def normalize_user_category_name(name)
+      name.to_s.downcase.gsub(/[^a-z0-9]/, " ").strip
+    end
+end
diff --git a/app/models/provider/plaid/category_taxonomy.rb b/app/models/provider/plaid/category_taxonomy.rb
new file mode 100644
index 00000000..9766c724
--- /dev/null
+++ b/app/models/provider/plaid/category_taxonomy.rb
@@ -0,0 +1,461 @@
+# https://plaid.com/documents/transactions-personal-finance-category-taxonomy.csv
+module Provider::Plaid::CategoryTaxonomy
+  CATEGORIES_MAP = {
+    income: {
+      classification: :income,
+      aliases: [ "income", "revenue", "earnings" ],
+      detailed_categories: {
+        income_dividends: {
+          classification: :income,
+          aliases: [ "dividend", "stock income", "dividend income", "dividend earnings" ]
+        },
+        income_interest_earned: {
+          classification: :income,
+          aliases: [ "interest", "bank interest", "interest earned", "interest income" ]
+        },
+        income_retirement_pension: {
+          classification: :income,
+          aliases: [ "retirement", "pension" ]
+        },
+        income_tax_refund: {
+          classification: :income,
+          aliases: [ "tax refund" ]
+        },
+        income_unemployment: {
+          classification: :income,
+          aliases: [ "unemployment" ]
+        },
+        income_wages: {
+          classification: :income,
+          aliases: [ "wage", "salary", "paycheck" ]
+        },
+        income_other_income: {
+          classification: :income,
+          aliases: [ "other income", "misc income" ]
+        }
+      }
+    },
+    loan_payments: {
+      classification: :expense,
+      aliases: [ "loan payment", "debt payment", "loan", "debt", "payment" ],
+      detailed_categories: {
+        loan_payments_car_payment: {
+          classification: :expense,
+          aliases: [ "car payment", "auto loan" ]
+        },
+        loan_payments_credit_card_payment: {
+          classification: :expense,
+          aliases: [ "credit card", "card payment" ]
+        },
+        loan_payments_personal_loan_payment: {
+          classification: :expense,
+          aliases: [ "personal loan", "loan payment" ]
+        },
+        loan_payments_mortgage_payment: {
+          classification: :expense,
+          aliases: [ "mortgage", "home loan" ]
+        },
+        loan_payments_student_loan_payment: {
+          classification: :expense,
+          aliases: [ "student loan", "education loan" ]
+        },
+        loan_payments_other_payment: {
+          classification: :expense,
+          aliases: [ "loan", "loan payment" ]
+        }
+      }
+    },
+    bank_fees: {
+      classification: :expense,
+      aliases: [ "bank fee", "service charge", "fee", "misc fees" ],
+      detailed_categories: {
+        bank_fees_atm_fees: {
+          classification: :expense,
+          aliases: [ "atm fee", "withdrawal fee" ]
+        },
+        bank_fees_foreign_transaction_fees: {
+          classification: :expense,
+          aliases: [ "foreign fee", "international fee" ]
+        },
+        bank_fees_insufficient_funds: {
+          classification: :expense,
+          aliases: [ "nsf fee", "overdraft" ]
+        },
+        bank_fees_interest_charge: {
+          classification: :expense,
+          aliases: [ "interest charge", "finance charge" ]
+        },
+        bank_fees_overdraft_fees: {
+          classification: :expense,
+          aliases: [ "overdraft fee" ]
+        },
+        bank_fees_other_bank_fees: {
+          classification: :expense,
+          aliases: [ "bank fee", "service charge" ]
+        }
+      }
+    },
+    entertainment: {
+      classification: :expense,
+      aliases: [ "entertainment", "recreation" ],
+      detailed_categories: {
+        entertainment_casinos_and_gambling: {
+          classification: :expense,
+          aliases: [ "casino", "gambling" ]
+        },
+        entertainment_music_and_audio: {
+          classification: :expense,
+          aliases: [ "music", "concert" ]
+        },
+        entertainment_sporting_events_amusement_parks_and_museums: {
+          classification: :expense,
+          aliases: [ "event", "amusement", "museum" ]
+        },
+        entertainment_tv_and_movies: {
+          classification: :expense,
+          aliases: [ "movie", "streaming" ]
+        },
+        entertainment_video_games: {
+          classification: :expense,
+          aliases: [ "game", "gaming" ]
+        },
+        entertainment_other_entertainment: {
+          classification: :expense,
+          aliases: [ "entertainment", "recreation" ]
+        }
+      }
+    },
+    food_and_drink: {
+      classification: :expense,
+      aliases: [ "food", "dining", "food and drink", "food & drink" ],
+      detailed_categories: {
+        food_and_drink_beer_wine_and_liquor: {
+          classification: :expense,
+          aliases: [ "alcohol", "liquor", "beer", "wine", "bar", "pub" ]
+        },
+        food_and_drink_coffee: {
+          classification: :expense,
+          aliases: [ "coffee", "cafe", "coffee shop" ]
+        },
+        food_and_drink_fast_food: {
+          classification: :expense,
+          aliases: [ "fast food", "takeout" ]
+        },
+        food_and_drink_groceries: {
+          classification: :expense,
+          aliases: [ "grocery", "supermarket", "grocery store" ]
+        },
+        food_and_drink_restaurant: {
+          classification: :expense,
+          aliases: [ "restaurant", "dining" ]
+        },
+        food_and_drink_vending_machines: {
+          classification: :expense,
+          aliases: [ "vending" ]
+        },
+        food_and_drink_other_food_and_drink: {
+          classification: :expense,
+          aliases: [ "food", "drink" ]
+        }
+      }
+    },
+    general_merchandise: {
+      classification: :expense,
+      aliases: [ "shopping", "retail" ],
+      detailed_categories: {
+        general_merchandise_bookstores_and_newsstands: {
+          classification: :expense,
+          aliases: [ "book", "newsstand" ]
+        },
+        general_merchandise_clothing_and_accessories: {
+          classification: :expense,
+          aliases: [ "clothing", "apparel" ]
+        },
+        general_merchandise_convenience_stores: {
+          classification: :expense,
+          aliases: [ "convenience" ]
+        },
+        general_merchandise_department_stores: {
+          classification: :expense,
+          aliases: [ "department store" ]
+        },
+        general_merchandise_discount_stores: {
+          classification: :expense,
+          aliases: [ "discount store" ]
+        },
+        general_merchandise_electronics: {
+          classification: :expense,
+          aliases: [ "electronic", "computer" ]
+        },
+        general_merchandise_gifts_and_novelties: {
+          classification: :expense,
+          aliases: [ "gift", "souvenir" ]
+        },
+        general_merchandise_office_supplies: {
+          classification: :expense,
+          aliases: [ "office supply" ]
+        },
+        general_merchandise_online_marketplaces: {
+          classification: :expense,
+          aliases: [ "online shopping" ]
+        },
+        general_merchandise_pet_supplies: {
+          classification: :expense,
+          aliases: [ "pet supply", "pet food" ]
+        },
+        general_merchandise_sporting_goods: {
+          classification: :expense,
+          aliases: [ "sporting good", "sport" ]
+        },
+        general_merchandise_superstores: {
+          classification: :expense,
+          aliases: [ "superstore", "retail" ]
+        },
+        general_merchandise_tobacco_and_vape: {
+          classification: :expense,
+          aliases: [ "tobacco", "smoke" ]
+        },
+        general_merchandise_other_general_merchandise: {
+          classification: :expense,
+          aliases: [ "shopping", "merchandise" ]
+        }
+      }
+    },
+    home_improvement: {
+      classification: :expense,
+      aliases: [ "home", "house", "house renovation", "home improvement", "renovation" ],
+      detailed_categories: {
+        home_improvement_furniture: {
+          classification: :expense,
+          aliases: [ "furniture", "furnishing" ]
+        },
+        home_improvement_hardware: {
+          classification: :expense,
+          aliases: [ "hardware", "tool" ]
+        },
+        home_improvement_repair_and_maintenance: {
+          classification: :expense,
+          aliases: [ "repair", "maintenance" ]
+        },
+        home_improvement_security: {
+          classification: :expense,
+          aliases: [ "security", "alarm" ]
+        },
+        home_improvement_other_home_improvement: {
+          classification: :expense,
+          aliases: [ "home improvement", "renovation" ]
+        }
+      }
+    },
+    medical: {
+      classification: :expense,
+      aliases: [ "medical", "healthcare", "health" ],
+      detailed_categories: {
+        medical_dental_care: {
+          classification: :expense,
+          aliases: [ "dental", "dentist" ]
+        },
+        medical_eye_care: {
+          classification: :expense,
+          aliases: [ "eye", "optometrist" ]
+        },
+        medical_nursing_care: {
+          classification: :expense,
+          aliases: [ "nursing", "care" ]
+        },
+        medical_pharmacies_and_supplements: {
+          classification: :expense,
+          aliases: [ "pharmacy", "prescription" ]
+        },
+        medical_primary_care: {
+          classification: :expense,
+          aliases: [ "doctor", "medical" ]
+        },
+        medical_veterinary_services: {
+          classification: :expense,
+          aliases: [ "vet", "veterinary" ]
+        },
+        medical_other_medical: {
+          classification: :expense,
+          aliases: [ "medical", "healthcare" ]
+        }
+      }
+    },
+    personal_care: {
+      classification: :expense,
+      aliases: [ "personal care", "grooming" ],
+      detailed_categories: {
+        personal_care_gyms_and_fitness_centers: {
+          classification: :expense,
+          aliases: [ "gym", "fitness", "exercise", "sport" ]
+        },
+        personal_care_hair_and_beauty: {
+          classification: :expense,
+          aliases: [ "salon", "beauty" ]
+        },
+        personal_care_laundry_and_dry_cleaning: {
+          classification: :expense,
+          aliases: [ "laundry", "cleaning" ]
+        },
+        personal_care_other_personal_care: {
+          classification: :expense,
+          aliases: [ "personal care", "grooming" ]
+        }
+      }
+    },
+    general_services: {
+      classification: :expense,
+      aliases: [ "service", "professional service" ],
+      detailed_categories: {
+        general_services_accounting_and_financial_planning: {
+          classification: :expense,
+          aliases: [ "accountant", "financial advisor" ]
+        },
+        general_services_automotive: {
+          classification: :expense,
+          aliases: [ "auto repair", "mechanic", "vehicle", "car", "car care", "car maintenance", "vehicle maintenance" ]
+        },
+        general_services_childcare: {
+          classification: :expense,
+          aliases: [ "childcare", "daycare" ]
+        },
+        general_services_consulting_and_legal: {
+          classification: :expense,
+          aliases: [ "legal", "attorney" ]
+        },
+        general_services_education: {
+          classification: :expense,
+          aliases: [ "education", "tuition" ]
+        },
+        general_services_insurance: {
+          classification: :expense,
+          aliases: [ "insurance", "premium" ]
+        },
+        general_services_postage_and_shipping: {
+          classification: :expense,
+          aliases: [ "shipping", "postage" ]
+        },
+        general_services_storage: {
+          classification: :expense,
+          aliases: [ "storage" ]
+        },
+        general_services_other_general_services: {
+          classification: :expense,
+          aliases: [ "service" ]
+        }
+      }
+    },
+    government_and_non_profit: {
+      classification: :expense,
+      aliases: [ "government", "non-profit" ],
+      detailed_categories: {
+        government_and_non_profit_donations: {
+          classification: :expense,
+          aliases: [ "donation", "charity", "charitable", "charitable donation", "giving", "gifts and donations", "gifts & donations" ]
+        },
+        government_and_non_profit_government_departments_and_agencies: {
+          classification: :expense,
+          aliases: [ "government", "agency" ]
+        },
+        government_and_non_profit_tax_payment: {
+          classification: :expense,
+          aliases: [ "tax payment", "tax" ]
+        },
+        government_and_non_profit_other_government_and_non_profit: {
+          classification: :expense,
+          aliases: [ "government", "non-profit" ]
+        }
+      }
+    },
+    transportation: {
+      classification: :expense,
+      aliases: [ "transportation", "travel" ],
+      detailed_categories: {
+        transportation_bikes_and_scooters: {
+          classification: :expense,
+          aliases: [ "bike", "scooter" ]
+        },
+        transportation_gas: {
+          classification: :expense,
+          aliases: [ "gas", "fuel" ]
+        },
+        transportation_parking: {
+          classification: :expense,
+          aliases: [ "parking" ]
+        },
+        transportation_public_transit: {
+          classification: :expense,
+          aliases: [ "transit", "bus" ]
+        },
+        transportation_taxis_and_ride_shares: {
+          classification: :expense,
+          aliases: [ "taxi", "rideshare" ]
+        },
+        transportation_tolls: {
+          classification: :expense,
+          aliases: [ "toll" ]
+        },
+        transportation_other_transportation: {
+          classification: :expense,
+          aliases: [ "transportation", "travel" ]
+        }
+      }
+    },
+    travel: {
+      classification: :expense,
+      aliases: [ "travel", "vacation", "trip", "sabbatical" ],
+      detailed_categories: {
+        travel_flights: {
+          classification: :expense,
+          aliases: [ "flight", "airfare" ]
+        },
+        travel_lodging: {
+          classification: :expense,
+          aliases: [ "hotel", "lodging" ]
+        },
+        travel_rental_cars: {
+          classification: :expense,
+          aliases: [ "rental car" ]
+        },
+        travel_other_travel: {
+          classification: :expense,
+          aliases: [ "travel", "trip" ]
+        }
+      }
+    },
+    rent_and_utilities: {
+      classification: :expense,
+      aliases: [ "utilities", "housing", "house", "home", "rent", "rent & utilities" ],
+      detailed_categories: {
+        rent_and_utilities_gas_and_electricity: {
+          classification: :expense,
+          aliases: [ "utility", "electric" ]
+        },
+        rent_and_utilities_internet_and_cable: {
+          classification: :expense,
+          aliases: [ "internet", "cable" ]
+        },
+        rent_and_utilities_rent: {
+          classification: :expense,
+          aliases: [ "rent", "lease" ]
+        },
+        rent_and_utilities_sewage_and_waste_management: {
+          classification: :expense,
+          aliases: [ "sewage", "waste" ]
+        },
+        rent_and_utilities_telephone: {
+          classification: :expense,
+          aliases: [ "phone", "telephone" ]
+        },
+        rent_and_utilities_water: {
+          classification: :expense,
+          aliases: [ "water" ]
+        },
+        rent_and_utilities_other_utilities: {
+          classification: :expense,
+          aliases: [ "utility" ]
+        }
+      }
+    }
+  }
+end
diff --git a/app/models/provider/synth.rb b/app/models/provider/synth.rb
index e095d2be..ff75ff49 100644
--- a/app/models/provider/synth.rb
+++ b/app/models/provider/synth.rb
@@ -159,38 +159,9 @@ class Provider::Synth < Provider
     end
   end
 
-  # ================================
-  #           Transactions
-  # ================================
-
-  def enrich_transaction(description, amount: nil, date: nil, city: nil, state: nil, country: nil)
-    with_provider_response do
-      params = {
-        description: description,
-        amount: amount,
-        date: date,
-        city: city,
-        state: state,
-        country: country
-      }.compact
-
-      response = client.get("#{base_url}/enrich", params)
-
-      parsed = JSON.parse(response.body)
-
-      TransactionEnrichmentData.new(
-        name: parsed.dig("merchant"),
-        icon_url: parsed.dig("icon"),
-        category: parsed.dig("category")
-      )
-    end
-  end
-
   private
     attr_reader :api_key
 
-    TransactionEnrichmentData = Data.define(:name, :icon_url, :category)
-
     def base_url
       ENV["SYNTH_URL"] || "https://api.synthfinance.com"
     end
diff --git a/app/models/provider_merchant.rb b/app/models/provider_merchant.rb
new file mode 100644
index 00000000..7f677981
--- /dev/null
+++ b/app/models/provider_merchant.rb
@@ -0,0 +1,6 @@
+class ProviderMerchant < Merchant
+  enum :source, { plaid: "plaid", synth: "synth", ai: "ai" }
+
+  validates :name, uniqueness: { scope: [ :source ] }
+  validates :source, presence: true
+end
diff --git a/app/models/rule.rb b/app/models/rule.rb
new file mode 100644
index 00000000..db8a99ae
--- /dev/null
+++ b/app/models/rule.rb
@@ -0,0 +1,90 @@
+class Rule < ApplicationRecord
+  UnsupportedResourceTypeError = Class.new(StandardError)
+
+  belongs_to :family
+  has_many :conditions, dependent: :destroy
+  has_many :actions, dependent: :destroy
+
+  accepts_nested_attributes_for :conditions, allow_destroy: true
+  accepts_nested_attributes_for :actions, allow_destroy: true
+
+  validates :resource_type, presence: true
+  validate :no_nested_compound_conditions
+
+  # Every rule must have at least 1 action
+  validate :min_actions
+  validate :no_duplicate_actions
+
+  def action_executors
+    registry.action_executors
+  end
+
+  def condition_filters
+    registry.condition_filters
+  end
+
+  def registry
+    @registry ||= case resource_type
+    when "transaction"
+      Rule::Registry::TransactionResource.new(self)
+    else
+      raise UnsupportedResourceTypeError, "Unsupported resource type: #{resource_type}"
+    end
+  end
+
+  def affected_resource_count
+    matching_resources_scope.count
+  end
+
+  def apply(ignore_attribute_locks: false)
+    actions.each do |action|
+      action.apply(matching_resources_scope, ignore_attribute_locks: ignore_attribute_locks)
+    end
+  end
+
+  def apply_later(ignore_attribute_locks: false)
+    RuleJob.perform_later(self, ignore_attribute_locks: ignore_attribute_locks)
+  end
+
+  private
+    def matching_resources_scope
+      scope = registry.resource_scope
+
+      # 1. Prepare the query with joins required by conditions
+      conditions.each do |condition|
+        scope = condition.prepare(scope)
+      end
+
+      # 2. Apply the conditions to the query
+      conditions.each do |condition|
+        scope = condition.apply(scope)
+      end
+
+      scope
+    end
+
+    def min_actions
+      if actions.reject(&:marked_for_destruction?).empty?
+        errors.add(:base, "must have at least one action")
+      end
+    end
+
+    def no_duplicate_actions
+      action_types = actions.reject(&:marked_for_destruction?).map(&:action_type)
+
+      errors.add(:base, "Rule cannot have duplicate actions #{action_types.inspect}") if action_types.uniq.count != action_types.count
+    end
+
+    # Validation: To keep rules simple and easy to understand, we don't allow nested compound conditions.
+    def no_nested_compound_conditions
+      return true if conditions.none? { |condition| condition.compound? }
+
+      conditions.each do |condition|
+        if condition.compound?
+          if condition.sub_conditions.any? { |sub_condition| sub_condition.compound? }
+            errors.add(:base, "Compound conditions cannot be nested")
+          end
+        end
+      end
+    end
+end
diff --git a/app/models/rule/action.rb b/app/models/rule/action.rb
new file mode 100644
index 00000000..00b66e2c
--- /dev/null
+++ b/app/models/rule/action.rb
@@ -0,0 +1,17 @@
+class Rule::Action < ApplicationRecord
+  belongs_to :rule
+
+  validates :action_type, presence: true
+
+  def apply(resource_scope, ignore_attribute_locks: false)
+    executor.execute(resource_scope, value: value, ignore_attribute_locks: ignore_attribute_locks)
+  end
+
+  def options
+    executor.options
+  end
+
+  def executor
+    rule.registry.get_executor!(action_type)
+  end
+end
diff --git a/app/models/rule/action_executor.rb b/app/models/rule/action_executor.rb
new file mode 100644
index 00000000..807e6cea
--- /dev/null
+++ b/app/models/rule/action_executor.rb
@@ -0,0 +1,43 @@
+class Rule::ActionExecutor
+  TYPES = [ "select", "function" ]
+
+  def initialize(rule)
+    @rule = rule
+  end
+
+  def key
+    self.class.name.demodulize.underscore
+  end
+
+  def label
+    key.humanize
+  end
+
+  def type
+    "function"
+  end
+
+  def options
+    nil
+  end
+
+  def execute(scope, value: nil, ignore_attribute_locks: false)
+    raise NotImplementedError, "Action executor #{self.class.name} must implement #execute"
+  end
+
+  def as_json
+    {
+      type: type,
+      key: key,
+      label: label,
+      options: options
+    }
+  end
+
+  private
+    attr_reader :rule
+
+    def family
+      rule.family
+    end
+end
diff --git a/app/models/rule/action_executor/auto_categorize.rb b/app/models/rule/action_executor/auto_categorize.rb
new file mode 100644
index 00000000..72ff324e
--- /dev/null
+++ b/app/models/rule/action_executor/auto_categorize.rb
@@ -0,0 +1,23 @@
+class Rule::ActionExecutor::AutoCategorize < Rule::ActionExecutor
+  def label
+    if rule.family.self_hoster?
+      "Auto-categorize transactions with AI ($$)"
+    else
+      "Auto-categorize transactions"
+    end
+  end
+
+  def execute(transaction_scope, value: nil, ignore_attribute_locks: false)
+    enrichable_transactions = transaction_scope.enrichable(:category_id)
+
+    if enrichable_transactions.empty?
+      Rails.logger.info("No transactions to auto-categorize for #{rule.title} #{rule.id}")
+      return
+    end
+
+    enrichable_transactions.in_batches(of: 20).each_with_index do |transactions, idx|
+      Rails.logger.info("Scheduling auto-categorization for batch #{idx + 1} of #{enrichable_transactions.count}")
+      rule.family.auto_categorize_transactions_later(transactions)
+    end
+  end
+end
diff --git a/app/models/rule/action_executor/auto_detect_merchants.rb b/app/models/rule/action_executor/auto_detect_merchants.rb
new file mode 100644
index 00000000..cc523303
--- /dev/null
+++ b/app/models/rule/action_executor/auto_detect_merchants.rb
@@ -0,0 +1,23 @@
+class Rule::ActionExecutor::AutoDetectMerchants < Rule::ActionExecutor
+  def label
+    if rule.family.self_hoster?
+      "Auto-detect merchants with AI ($$)"
+    else
+      "Auto-detect merchants"
+    end
+  end
+
+  def execute(transaction_scope, value: nil, ignore_attribute_locks: false)
+    enrichable_transactions = transaction_scope.enrichable(:merchant_id)
+
+    if enrichable_transactions.empty?
+      Rails.logger.info("No transactions to auto-detect merchants for #{rule.title} #{rule.id}")
+      return
+    end
+
+    enrichable_transactions.in_batches(of: 20).each_with_index do |transactions, idx|
+      Rails.logger.info("Scheduling auto-merchant-enrichment for batch #{idx + 1} of #{enrichable_transactions.count}")
+      rule.family.auto_detect_transaction_merchants_later(transactions)
+    end
+  end
+end
diff --git a/app/models/rule/action_executor/set_transaction_category.rb b/app/models/rule/action_executor/set_transaction_category.rb
new file mode 100644
index 00000000..ef186d96
--- /dev/null
+++ b/app/models/rule/action_executor/set_transaction_category.rb
@@ -0,0 +1,31 @@
+class Rule::ActionExecutor::SetTransactionCategory < Rule::ActionExecutor
+  def type
+    "select"
+  end
+
+  def options
+    family.categories.pluck(:name, :id)
+  end
+
+  def execute(transaction_scope, value: nil, ignore_attribute_locks: false)
+    category = family.categories.find_by_id(value)
+
+    scope = transaction_scope
+
+    unless ignore_attribute_locks
+      scope = scope.enrichable(:category_id)
+    end
+
+    scope.each do |txn|
+      Rule.transaction do
+        txn.log_enrichment!(
+          attribute_name: "category_id",
+          attribute_value: category.id,
+          source: "rule"
+        )
+
+        txn.update!(category: category)
+      end
+    end
+  end
+end
diff --git a/app/models/rule/action_executor/set_transaction_tags.rb b/app/models/rule/action_executor/set_transaction_tags.rb
new file mode 100644
index 00000000..4d539496
--- /dev/null
+++ b/app/models/rule/action_executor/set_transaction_tags.rb
@@ -0,0 +1,31 @@
+class Rule::ActionExecutor::SetTransactionTags < Rule::ActionExecutor
+  def type
+    "select"
+  end
+
+  def options
+    family.tags.pluck(:name, :id)
+  end
+
+  def execute(transaction_scope, value: nil, ignore_attribute_locks: false)
+    tag = family.tags.find_by_id(value)
+
+    scope = transaction_scope
+
+    unless ignore_attribute_locks
+      scope = scope.enrichable(:tag_ids)
+    end
+
+    rows = scope.each do |txn|
+      Rule.transaction do
+        txn.log_enrichment!(
+          attribute_name: "tag_ids",
+          attribute_value: [ tag.id ],
+          source: "rule"
+        )
+
+        txn.update!(tag_ids: [ tag.id ])
+      end
+    end
+  end
+end
diff --git a/app/models/rule/condition.rb b/app/models/rule/condition.rb
new file mode 100644
index 00000000..e15115fe
--- /dev/null
+++ b/app/models/rule/condition.rb
@@ -0,0 +1,62 @@
+class Rule::Condition < ApplicationRecord
+  belongs_to :rule, optional: -> { where.not(parent_id: nil) }
+  belongs_to :parent, class_name: "Rule::Condition", optional: true, inverse_of: :sub_conditions
+
+  has_many :sub_conditions, class_name: "Rule::Condition", foreign_key: :parent_id, dependent: :destroy, inverse_of: :parent
+
+  validates :condition_type, presence: true
+  validates :operator, presence: true
+  validates :value, presence: true, unless: -> { compound? }
+
+  accepts_nested_attributes_for :sub_conditions, allow_destroy: true
+
+  # We don't store rule_id on sub_conditions, so "walk up" to the parent rule
+  def rule
+    parent&.rule || super
+  end
+
+  def compound?
+    condition_type == "compound"
+  end
+
+  def apply(scope)
+    if compound?
+      build_compound_scope(scope)
+    else
+      filter.apply(scope, operator, value)
+    end
+  end
+
+  def prepare(scope)
+    if compound?
+      sub_conditions.reduce(scope) { |s, sub| sub.prepare(s) }
+    else
+      filter.prepare(scope)
+    end
+  end
+
+  def options
+    filter.options
+  end
+
+  def operators
+    filter.operators
+  end
+
+  def filter
+    rule.registry.get_filter!(condition_type)
+  end
+
+  private
+    def build_compound_scope(scope)
+      if operator == "or"
+        combined_scope = sub_conditions
+          .map { |sub| sub.apply(scope) }
+          .reduce { |acc, s| acc.or(s) }
+
+        combined_scope || scope
+      else
+        sub_conditions.reduce(scope) { |s, sub| sub.apply(s) }
+      end
+    end
+end
diff --git a/app/models/rule/condition_filter.rb b/app/models/rule/condition_filter.rb
new file mode 100644
index 00000000..86d40ea2
--- /dev/null
+++ b/app/models/rule/condition_filter.rb
@@ -0,0 +1,87 @@
+class Rule::ConditionFilter
+  UnsupportedOperatorError = Class.new(StandardError)
+
+  TYPES = [ "text", "number", "select" ]
+
+  OPERATORS_MAP = {
+    "text" => [ [ "Contains", "like" ], [ "Equal to", "=" ] ],
+    "number" => [ [ "Greater than", ">" ], [ "Greater or equal to", ">=" ], [ "Less than", "<" ], [ "Less than or equal to", "<=" ], [ "Is equal to", "=" ] ],
+    "select" => [ [ "Equal to", "=" ] ]
+  }
+
+  def initialize(rule)
+    @rule = rule
+  end
+
+  def type
+    "text"
+  end
+
+  def number_step
+    family_currency = Money::Currency.new(family.currency)
+    family_currency.step
+  end
+
+  def key
+    self.class.name.demodulize.underscore
+  end
+
+  def label
+    key.humanize
+  end
+
+  def options
+    nil
+  end
+
+  def operators
+    OPERATORS_MAP.dig(type)
+  end
+
+  # Matchers can prepare the scope with joins by implementing this method
+  def prepare(scope)
+    scope
+  end
+
+  # Applies the condition to the scope
+  def apply(scope, operator, value)
+    raise NotImplementedError, "Condition #{self.class.name} must implement #apply"
+  end
+
+  def as_json
+    {
+      type: type,
+      key: key,
+      label: label,
+      operators: operators,
+      options: options,
+      number_step: number_step
+    }
+  end
+
+  private
+    attr_reader :rule
+
+    def family
+      rule.family
+    end
+
+    def build_sanitized_where_condition(field, operator, value)
+      sanitized_value = operator == "like" ? "%#{ActiveRecord::Base.sanitize_sql_like(value)}%" : value
+
+      ActiveRecord::Base.sanitize_sql_for_conditions([
+        "#{field} #{sanitize_operator(operator)} ?",
+        sanitized_value
+      ])
+    end
+
+    def sanitize_operator(operator)
+      raise UnsupportedOperatorError, "Unsupported operator: #{operator} for type: #{type}" unless operators.map(&:last).include?(operator)
+
+      if operator == "like"
+        "ILIKE"
+      else
+        operator
+      end
+    end
+end
diff --git a/app/models/rule/condition_filter/transaction_amount.rb b/app/models/rule/condition_filter/transaction_amount.rb
new file mode 100644
index 00000000..5be1a9fb
--- /dev/null
+++ b/app/models/rule/condition_filter/transaction_amount.rb
@@ -0,0 +1,14 @@
+class Rule::ConditionFilter::TransactionAmount < Rule::ConditionFilter
+  def type
+    "number"
+  end
+
+  def prepare(scope)
+    scope.with_entry
+  end
+
+  def apply(scope, operator, value)
+    expression = build_sanitized_where_condition("ABS(entries.amount)", operator, value.to_d)
+    scope.where(expression)
+  end
+end
diff --git a/app/models/rule/condition_filter/transaction_merchant.rb b/app/models/rule/condition_filter/transaction_merchant.rb
new file mode 100644
index 00000000..db152226
--- /dev/null
+++ b/app/models/rule/condition_filter/transaction_merchant.rb
@@ -0,0 +1,18 @@
+class Rule::ConditionFilter::TransactionMerchant < Rule::ConditionFilter
+  def type
+    "select"
+  end
+
+  def options
+    family.assigned_merchants.pluck(:name, :id)
+  end
+
+  def prepare(scope)
+    scope.left_joins(:merchant)
+  end
+
+  def apply(scope, operator, value)
+    expression = build_sanitized_where_condition("merchants.id", operator, value)
+    scope.where(expression)
+  end
+end
diff --git a/app/models/rule/condition_filter/transaction_name.rb b/app/models/rule/condition_filter/transaction_name.rb
new file mode 100644
index 00000000..c1b3baf7
--- /dev/null
+++ b/app/models/rule/condition_filter/transaction_name.rb
@@ -0,0 +1,10 @@
+class Rule::ConditionFilter::TransactionName < Rule::ConditionFilter
+  def prepare(scope)
+    scope.with_entry
+  end
+
+  def apply(scope, operator, value)
+    expression = build_sanitized_where_condition("entries.name", operator, value)
+    scope.where(expression)
+  end
+end
diff --git a/app/models/rule/registry.rb b/app/models/rule/registry.rb
new file mode 100644
index 00000000..4c3f80cf
--- /dev/null
+++ b/app/models/rule/registry.rb
@@ -0,0 +1,46 @@
+class Rule::Registry
+  UnsupportedActionError = Class.new(StandardError)
+  UnsupportedConditionError = Class.new(StandardError)
+
+  def initialize(rule)
+    @rule = rule
+  end
+
+  def resource_scope
+    raise NotImplementedError, "#{self.class.name} must implement #resource_scope"
+  end
+
+  def condition_filters
+    []
+  end
+
+  def action_executors
+    []
+  end
+
+  def get_filter!(key)
+    filter = condition_filters.find { |filter| filter.key == key }
+    raise UnsupportedConditionError, "Unsupported condition type: #{key}" unless filter
+    filter
+  end
+
+  def get_executor!(key)
+    executor = action_executors.find { |executor| executor.key == key }
+    raise UnsupportedActionError, "Unsupported action type: #{key}" unless executor
+    executor
+  end
+
+  def as_json
+    {
+      filters: condition_filters.map(&:as_json),
+      executors: action_executors.map(&:as_json)
+    }
+  end
+
+  private
+    attr_reader :rule
+
+    def family
+      rule.family
+    end
+end
diff --git a/app/models/rule/registry/transaction_resource.rb b/app/models/rule/registry/transaction_resource.rb
new file mode 100644
index 00000000..1bcdf8a7
--- /dev/null
+++ b/app/models/rule/registry/transaction_resource.rb
@@ -0,0 +1,32 @@
+class Rule::Registry::TransactionResource < Rule::Registry
+  def resource_scope
+    family.transactions.active.with_entry.where(entry: { date: rule.effective_date.. })
+  end
+
+  def condition_filters
+    [
+      Rule::ConditionFilter::TransactionName.new(rule),
+      Rule::ConditionFilter::TransactionAmount.new(rule),
+      Rule::ConditionFilter::TransactionMerchant.new(rule)
+    ]
+  end
+
+  def action_executors
+    enabled_executors = [
+      Rule::ActionExecutor::SetTransactionCategory.new(rule),
+      Rule::ActionExecutor::SetTransactionTags.new(rule)
+    ]
+
+    if ai_enabled?
+      enabled_executors << Rule::ActionExecutor::AutoCategorize.new(rule)
+      enabled_executors << Rule::ActionExecutor::AutoDetectMerchants.new(rule)
+    end
+
+    enabled_executors
+  end
+
+  private
+    def ai_enabled?
+      Provider::Registry.get_provider(:openai).present?
+    end
+end
diff --git a/app/models/sync.rb b/app/models/sync.rb
index 75718d0b..04141570 100644
--- a/app/models/sync.rb
+++ b/app/models/sync.rb
@@ -23,19 +23,19 @@ class Sync < ApplicationRecord
         update!(data: data) if data
 
         complete! unless has_pending_child_syncs?
-      rescue StandardError => error
-        fail! error
-        raise error if Rails.env.development?
-      ensure
+
         Rails.logger.info("Sync completed, starting post-sync")
 
+        syncable.post_sync(self) unless has_pending_child_syncs?
+
         if has_parent?
           notify_parent_of_completion!
-        else
-          syncable.post_sync(self)
         end
 
         Rails.logger.info("Post-sync completed")
+      rescue StandardError => error
+        fail! error
+        raise error if Rails.env.development?
       end
     end
   end
diff --git a/app/models/trade_builder.rb b/app/models/trade_builder.rb
index 9b7e0471..4f0019b9 100644
--- a/app/models/trade_builder.rb
+++ b/app/models/trade_builder.rb
@@ -15,6 +15,21 @@ class TradeBuilder
     buildable.save
   end
 
+  def lock_saved_attributes!
+    if buildable.is_a?(Transfer)
+      buildable.inflow_transaction.entry.lock_saved_attributes!
+      buildable.outflow_transaction.entry.lock_saved_attributes!
+    else
+      buildable.lock_saved_attributes!
+    end
+  end
+
+  def entryable
+    return nil if buildable.is_a?(Transfer)
+
+    buildable.entryable
+  end
+
   def errors
     buildable.errors
   end
diff --git a/app/models/transaction.rb b/app/models/transaction.rb
index fb5fb0df..d2a8abdc 100644
--- a/app/models/transaction.rb
+++ b/app/models/transaction.rb
@@ -1,5 +1,5 @@
 class Transaction < ApplicationRecord
-  include Entryable, Transferable, Provided
+  include Entryable, Transferable, Ruleable
 
   belongs_to :category, optional: true
   belongs_to :merchant, optional: true
@@ -14,4 +14,14 @@ class Transaction < ApplicationRecord
       Search.new(params).build_query(all)
     end
   end
+
+  def set_category!(category)
+    if category.is_a?(String)
+      category = entry.account.family.categories.find_or_create_by!(
+        name: category
+      )
+    end
+
+    update!(category: category)
+  end
 end
diff --git a/app/models/transaction/provided.rb b/app/models/transaction/provided.rb
deleted file mode 100644
index b4210e0a..00000000
--- a/app/models/transaction/provided.rb
+++ /dev/null
@@ -1,20 +0,0 @@
-module Transaction::Provided
-  extend ActiveSupport::Concern
-
-  def fetch_enrichment_info
-    return nil unless provider
-
-    response = provider.enrich_transaction(
-      entry.name,
-      amount: entry.amount,
-      date: entry.date
-    )
-
-    response.data
-  end
-
-  private
-    def provider
-      Provider::Registry.get_provider(:synth)
-    end
-end
diff --git a/app/models/transaction/ruleable.rb b/app/models/transaction/ruleable.rb
new file mode 100644
index 00000000..aacd1b92
--- /dev/null
+++ b/app/models/transaction/ruleable.rb
@@ -0,0 +1,17 @@
+module Transaction::Ruleable
+  extend ActiveSupport::Concern
+
+  def eligible_for_category_rule?
+    rules.joins(:actions).where(
+      actions: {
+        action_type: "set_transaction_category",
+        value: category_id
+      }
+    ).empty?
+  end
+
+  private
+    def rules
+      entry.account.family.rules
+    end
+end
diff --git a/app/models/transfer.rb b/app/models/transfer.rb
index d681d581..601966bb 100644
--- a/app/models/transfer.rb
+++ b/app/models/transfer.rb
@@ -29,7 +29,6 @@ class Transfer < ApplicationRecord
             currency: converted_amount.currency.iso_code,
             date: date,
             name: "Transfer from #{from_account.name}",
-            entryable: Transaction.new
           )
         ),
         outflow_transaction: Transaction.new(
@@ -38,7 +37,6 @@ class Transfer < ApplicationRecord
             currency: from_account.currency,
             date: date,
             name: "Transfer to #{to_account.name}",
-            entryable: Transaction.new
           )
         ),
         status: "confirmed"
diff --git a/app/views/accounts/_account.html.erb b/app/views/accounts/_account.html.erb
index 80ad5a07..afbd6fb3 100644
--- a/app/views/accounts/_account.html.erb
+++ b/app/views/accounts/_account.html.erb
@@ -32,14 +32,7 @@
       </p>
 
       <% unless account.scheduled_for_deletion? %>
-        <%= form_with model: account,
-                    namespace: account.id,
-                    data: { controller: "auto-submit-form", turbo_frame: "_top" } do |form| %>
-          <div class="relative inline-block select-none">
-            <%= form.check_box :is_active, { class: "sr-only peer", data: { "auto-submit-form-target": "auto" } } %>
-            <%= form.label :is_active, "&nbsp;".html_safe, class: "switch" %>
-          </div>
-        <% end %>
+        <%= render "shared/toggle_form", model: account, attribute: :is_active, turbo_frame: "_top" %>
       <% end %>
     </div>
   </div>
diff --git a/app/views/budget_categories/_no_categories.html.erb b/app/views/budget_categories/_no_categories.html.erb
index 8755d0b8..5f489f94 100644
--- a/app/views/budget_categories/_no_categories.html.erb
+++ b/app/views/budget_categories/_no_categories.html.erb
@@ -6,7 +6,7 @@
     </p>
 
     <div class="flex items-center gap-2">
-      <%= button_to "Use default categories", bootstrap_categories_path, class: "btn btn--primary" %>
+      <%= button_to "Use defaults (recommended)", bootstrap_categories_path, class: "btn btn--primary" %>
 
       <%= link_to new_category_path, class: "btn btn--outline flex items-center gap-1", data: { turbo_frame: "modal" } do %>
         <%= lucide_icon("plus", class: "w-5 h-5") %>
diff --git a/app/views/categories/_category.html.erb b/app/views/categories/_category.html.erb
index d3e25261..f04e1e96 100644
--- a/app/views/categories/_category.html.erb
+++ b/app/views/categories/_category.html.erb
@@ -10,20 +10,18 @@
   </div>
   <div class="justify-self-end">
     <%= contextual_menu do %>
-      <div class="w-48 p-1 text-sm leading-6 text-primary bg-container shadow-lg shrink rounded-xl ring-1 ring-gray-900/5">
-        <%= contextual_menu_modal_action_item t(".edit"), edit_category_path(category) %>
+      <%= contextual_menu_modal_action_item t(".edit"), edit_category_path(category) %>
 
-        <% if category.transactions.any? %>
-          <%= link_to new_category_deletion_path(category),
+      <% if category.transactions.any? %>
+        <%= link_to new_category_deletion_path(category),
               class: "flex items-center w-full rounded-lg text-red-600 hover:bg-red-50 py-2 px-3 gap-2",
               data: { turbo_frame: :modal } do %>
-            <%= lucide_icon "trash-2", class: "shrink-0 w-5 h-5" %>
-            <span class="text-sm"><%= t(".delete") %></span>
-          <% end %>
-        <% else %>
-          <%= contextual_menu_destructive_item t(".delete"), category_path(category), turbo_confirm: nil %>
+          <%= lucide_icon "trash-2", class: "shrink-0 w-5 h-5" %>
+          <span class="text-sm"><%= t(".delete") %></span>
         <% end %>
-      </div>
+      <% else %>
+        <%= contextual_menu_destructive_item t(".delete"), category_path(category), turbo_confirm: nil %>
+      <% end %>
     <% end %>
   </div>
 </div>
diff --git a/app/views/categories/edit.html.erb b/app/views/categories/edit.html.erb
index e577bb5e..43daea2d 100644
--- a/app/views/categories/edit.html.erb
+++ b/app/views/categories/edit.html.erb
@@ -1,3 +1,3 @@
-<%= modal_form_wrapper title: t(".edit") do %>
+<%= modal_form_wrapper title: t(".edit"), overflow_visible: true do %>
   <%= render "form", category: @category, categories: @categories %>
 <% end %>
diff --git a/app/views/categories/index.html.erb b/app/views/categories/index.html.erb
index 21ecc95a..fec33344 100644
--- a/app/views/categories/index.html.erb
+++ b/app/views/categories/index.html.erb
@@ -1,11 +1,20 @@
-
 <header class="flex items-center justify-between">
   <h1 class="text-primary text-xl font-medium"><%= t(".categories") %></h1>
 
-  <%= link_to new_category_path, class: "btn btn--primary flex items-center gap-1 justify-center", data: { turbo_frame: :modal } do %>
-    <%= lucide_icon "plus", class: "w-5 h-5" %>
-    <p><%= t(".new") %></p>
-  <% end %>
+  <div class="flex items-center gap-2">
+    <%= contextual_menu do %>
+      <%= contextual_menu_destructive_item "Delete all", destroy_all_categories_path, turbo_confirm: {
+        title: "Delete all categories?",
+        body: "All of your transactions will become uncategorized and this cannot be undone.",
+        accept: "Delete all categories",
+      } %>
+    <% end %>
+
+    <%= link_to new_category_path, class: "btn btn--primary flex items-center gap-1 justify-center", data: { turbo_frame: :modal } do %>
+      <%= lucide_icon "plus", class: "w-5 h-5" %>
+      <p><%= t(".new") %></p>
+    <% end %>
+  </div>
 </header>
 
 <div class="bg-container shadow-border-xs rounded-xl p-4">
diff --git a/app/views/categories/new.html.erb b/app/views/categories/new.html.erb
index 2d100b49..6478d94d 100644
--- a/app/views/categories/new.html.erb
+++ b/app/views/categories/new.html.erb
@@ -1,3 +1,3 @@
-<%= modal_form_wrapper title: t(".new_category") do %>
+<%= modal_form_wrapper title: t(".new_category"), overflow_visible: true do %>
   <%= render "form", category: @category, categories: @categories %>
 <% end %>
diff --git a/app/views/chats/index.html.erb b/app/views/chats/index.html.erb
index bf10a596..8eb610b7 100644
--- a/app/views/chats/index.html.erb
+++ b/app/views/chats/index.html.erb
@@ -7,7 +7,7 @@
       <% end %>
     </nav>
 
-    <div class="grow">
+    <div class="grow flex flex-col">
       <h1 class="text-xl font-medium mb-6">Chats</h1>
 
       <% if @chats.any? %>
@@ -22,7 +22,7 @@
           <h3 class="text-lg font-medium text-primary mb-1">No chats yet</h3>
           <p class="text-gray-500 mb-4">Start a new conversation with the AI assistant</p>
         </div>
-        <div class="mt-auto p-4">
+        <div class="mt-auto p-4 lg:mt-auto">
           <%= render "messages/chat_form", chat: nil %>
         </div>
       <% end %>
diff --git a/app/views/chats/show.html.erb b/app/views/chats/show.html.erb
index 28f9b8c1..341eca01 100644
--- a/app/views/chats/show.html.erb
+++ b/app/views/chats/show.html.erb
@@ -28,7 +28,7 @@
       <% end %>
     </div>
 
-    <div class="p-4">
+    <div class="p-4 lg:mt-auto">
       <%= render "messages/chat_form", chat: @chat %>
     </div>
   </div>
diff --git a/app/views/family_merchants/_family_merchant.html.erb b/app/views/family_merchants/_family_merchant.html.erb
new file mode 100644
index 00000000..ec1cc1fd
--- /dev/null
+++ b/app/views/family_merchants/_family_merchant.html.erb
@@ -0,0 +1,31 @@
+<%# locals: (family_merchant:) %>
+
+<div class="flex justify-between items-center p-4 bg-white">
+  <div class="flex w-full items-center gap-2.5">
+    <% if family_merchant.logo_url %>
+      <div class="w-8 h-8 rounded-full flex justify-center items-center">
+        <%= image_tag family_merchant.logo_url, class: "w-8 h-8 rounded-full" %>
+      </div>
+    <% else %>
+      <%= render partial: "shared/color_avatar", locals: { name: family_merchant.name, color: family_merchant.color } %>
+    <% end %>
+
+    <p class="text-primary text-sm truncate">
+      <%= family_merchant.name %>
+    </p>
+  </div>
+  <div class="justify-self-end">
+    <%= contextual_menu do %>
+      <%= contextual_menu_modal_action_item t(".edit"), edit_family_merchant_path(family_merchant), icon: "pencil", turbo_frame: "modal" %>
+
+      <%= contextual_menu_destructive_item "Delete",
+                                             family_merchant_path(family_merchant),
+                                             turbo_frame: "_top",
+                                             turbo_confirm: family_merchant.transactions.any? ? {
+                                               title: "Delete #{family_merchant.name}?",
+                                               body: "This will remove this merchant from all transactions it has been assigned to.",
+                                               accept: "Delete"
+                                             } : nil %>
+    <% end %>
+  </div>
+</div>
diff --git a/app/views/merchants/_form.html.erb b/app/views/family_merchants/_form.html.erb
similarity index 77%
rename from app/views/merchants/_form.html.erb
rename to app/views/family_merchants/_form.html.erb
index 93efecb9..baaec60a 100644
--- a/app/views/merchants/_form.html.erb
+++ b/app/views/family_merchants/_form.html.erb
@@ -1,11 +1,14 @@
 <div data-controller="color-avatar">
-  <%= styled_form_with model: @merchant, class: "space-y-4", data: { turbo_frame: :_top } do |f| %>
+  <%= styled_form_with model: @merchant, class: "space-y-4" do |f| %>
     <section class="space-y-4">
-      <div class="w-fit m-auto">
+      <% if @merchant.errors.any? %>
+        <%= render "shared/form_errors", model: @merchant %>
+      <% end %>
+      <div class="w-fit m-auto mb-4">
         <%= render partial: "shared/color_avatar", locals: { name: @merchant.name, color: @merchant.color } %>
       </div>
       <div class="flex gap-2 items-center justify-center">
-        <% Merchant::COLORS.each do |color| %>
+        <% FamilyMerchant::COLORS.each do |color| %>
           <label class="relative">
             <%= f.radio_button :color, color, class: "sr-only peer", data: { action: "change->color-avatar#handleColorChange" } %>
             <div class="w-6 h-6 rounded-full cursor-pointer peer-checked:ring-2 peer-checked:ring-offset-2 peer-checked:ring-blue-500" style="background-color: <%= color %>"></div>
diff --git a/app/views/merchants/_ruler.html.erb b/app/views/family_merchants/_ruler.html.erb
similarity index 100%
rename from app/views/merchants/_ruler.html.erb
rename to app/views/family_merchants/_ruler.html.erb
diff --git a/app/views/merchants/edit.html.erb b/app/views/family_merchants/edit.html.erb
similarity index 100%
rename from app/views/merchants/edit.html.erb
rename to app/views/family_merchants/edit.html.erb
diff --git a/app/views/merchants/index.html.erb b/app/views/family_merchants/index.html.erb
similarity index 62%
rename from app/views/merchants/index.html.erb
rename to app/views/family_merchants/index.html.erb
index 6a91e423..4f72e455 100644
--- a/app/views/merchants/index.html.erb
+++ b/app/views/family_merchants/index.html.erb
@@ -1,9 +1,9 @@
 <header class="flex items-center justify-between">
-  <h1 class="text-primary text-xl font-medium"><%= t(".title") %></h1>
+  <h1 class="text-primary text-xl font-medium">Merchants</h1>
 
-  <%= link_to new_merchant_path, class: "btn btn--primary flex items-center gap-1 justify-center", data: { turbo_frame: :modal } do %>
-    <%= lucide_icon "plus", class: "w-5 h-5" %>
-    <p><%= t(".new") %></p>
+  <%= link_to new_family_merchant_path, class: "btn btn--primary flex items-center gap-2", data: { turbo_frame: "modal" } do %>
+    <%= lucide_icon("plus", class: "w-5 h-5") %>
+    <p class="text-sm font-medium">New merchant</p>
   <% end %>
 </header>
 
@@ -18,7 +18,7 @@
 
       <div class="border border-alpha-black-25 rounded-md bg-container shadow-border-xs">
         <div class="overflow-hidden rounded-md">
-          <%= render partial: @merchants, spacer_template: "merchants/ruler" %>
+          <%= render partial: "family_merchants/family_merchant", collection: @merchants, spacer_template: "family_merchants/ruler" %>
         </div>
       </div>
     </div>
@@ -26,7 +26,7 @@
     <div class="flex justify-center items-center py-20">
       <div class="text-center flex flex-col items-center max-w-[300px]">
         <p class="text-primary mb-1 font-medium text-sm"><%= t(".empty") %></p>
-        <%= link_to new_merchant_path, class: "w-fit flex text-white text-sm font-medium items-center gap-1 bg-gray-900 rounded-lg p-2 pr-3", data: { turbo_frame: "modal" } do %>
+        <%= link_to new_family_merchant_path, class: "w-fit flex text-white text-sm font-medium items-center gap-1 bg-gray-900 rounded-lg p-2 pr-3", data: { turbo_frame: "modal" } do %>
           <%= lucide_icon("plus", class: "w-5 h-5") %>
           <span><%= t(".new") %></span>
         <% end %>
diff --git a/app/views/merchants/new.html.erb b/app/views/family_merchants/new.html.erb
similarity index 100%
rename from app/views/merchants/new.html.erb
rename to app/views/family_merchants/new.html.erb
diff --git a/app/views/layouts/application.html.erb b/app/views/layouts/application.html.erb
index b61c6588..846a656c 100644
--- a/app/views/layouts/application.html.erb
+++ b/app/views/layouts/application.html.erb
@@ -5,56 +5,58 @@
        data-controller="sidebar"
        data-sidebar-user-id-value="<%= Current.user.id %>"
        data-sidebar-config-value="<%= sidebar_config.to_json %>">
+    <button hidden data-controller="hotkey" data-hotkey="b" data-action="sidebar#toggleLeftPanel">Toggle accounts</button>
+    <button hidden data-controller="hotkey" data-hotkey="l" data-action="sidebar#toggleRightPanel">Toggle chat</button>
+
     <% unless controller_name == 'chats' %>
-    <nav class="flex justify-between lg:justify-start lg:flex-col shrink-0 lg:w-[84px] p-3 lg:px-0 lg:py-4 lg:mr-3">
+      <nav class="flex justify-between lg:justify-start lg:flex-col shrink-0 lg:w-[84px] p-3 lg:px-0 lg:py-4 lg:mr-3">
+        <button data-action="sidebar#toggleLeftPanelMobile" class="lg:hidden inline-flex p-2 rounded-lg items-center justify-center hover:bg-gray-100 cursor-pointer">
+          <%= icon("panel-left", color: "gray") %>
+        </button>
 
-      <button data-action="sidebar#toggleLeftPanelMobile" class="lg:hidden inline-flex p-2 rounded-lg items-center justify-center hover:bg-gray-100 cursor-pointer">
-        <%= icon("panel-left", color: "gray") %>
-      </button>
-
-      <%# Mobile only account sidebar groups %>
-      <%= tag.div class: class_names("hidden bg-surface z-20 absolute inset-0 h-dvh w-full p-4 overflow-y-auto transition-all duration-300 pt-safe"),
+        <%# Mobile only account sidebar groups %>
+        <%= tag.div class: class_names("hidden bg-surface z-20 absolute inset-0 h-dvh w-full p-4 overflow-y-auto transition-all duration-300 pt-safe"),
                   data: { sidebar_target: "leftPanelMobile" } do %>
-        <div id="account-sidebar-tabs">
-          <div class="mb-4">
-            <button data-action="sidebar#toggleLeftPanelMobile">
-              <%= icon("x", color: "gray") %>
-            </button>
+          <div id="account-sidebar-tabs" class="pt-6">
+            <div class="mb-4">
+              <button data-action="sidebar#toggleLeftPanelMobile">
+                <%= icon("x", color: "gray") %>
+              </button>
+            </div>
+            <%= render "accounts/account_sidebar_tabs", family: Current.family %>
           </div>
-          <%= render "accounts/account_sidebar_tabs", family: Current.family %>
-        </div>
-      <% end %>
-
-      <div class="lg:pl-2 lg:mb-3">
-        <%= link_to root_path, class: "block" do %>
-          <%= image_tag "logomark-color.svg", class: "w-9 h-9 mx-auto" %>
         <% end %>
-      </div>
 
-      <ul class="space-y-0.5 hidden lg:block">
-        <li>
-          <%= render "layouts/sidebar/nav_item", name: "Home", path: root_path, icon_key: "pie-chart" %>
-        </li>
-
-        <li>
-          <%= render "layouts/sidebar/nav_item", name: "Transactions", path: transactions_path, icon_key: "credit-card" %>
-        </li>
-
-        <li>
-          <%= render "layouts/sidebar/nav_item", name: "Budgets", path: budgets_path, icon_key: "map" %>
-        </li>
-      </ul>
-
-      <div class="lg:pl-2 lg:mt-auto lg:mx-auto">
-        <div class="lg:hidden">
-          <%= render "users/user_menu", user: Current.user, placement: "bottom-end", offset: 12 %>
+        <div class="lg:pl-2 lg:mb-3">
+          <%= link_to root_path, class: "block" do %>
+            <%= image_tag "logomark-color.svg", class: "w-9 h-9 mx-auto" %>
+          <% end %>
         </div>
 
-        <div class="hidden lg:block">
-          <%= render "users/user_menu", user: Current.user %>
+        <ul class="space-y-0.5 hidden lg:block">
+          <li>
+            <%= render "layouts/sidebar/nav_item", name: "Home", path: root_path, icon_key: "pie-chart" %>
+          </li>
+
+          <li>
+            <%= render "layouts/sidebar/nav_item", name: "Transactions", path: transactions_path, icon_key: "credit-card" %>
+          </li>
+
+          <li>
+            <%= render "layouts/sidebar/nav_item", name: "Budgets", path: budgets_path, icon_key: "map" %>
+          </li>
+        </ul>
+
+        <div class="lg:pl-2 lg:mt-auto lg:mx-auto">
+          <div class="lg:hidden">
+            <%= render "users/user_menu", user: Current.user, placement: "bottom-end", offset: 12 %>
+          </div>
+
+          <div class="hidden lg:block">
+            <%= render "users/user_menu", user: Current.user %>
+          </div>
         </div>
-      </div>
-    </nav>
+      </nav>
     <% end %>
 
     <div class="flex justify-between lg:justify-normal grow overflow-y-auto">
@@ -110,7 +112,7 @@
       <% end %>
     </div>
 
-    <nav class="lg:hidden bg-surface md:bg-container shrink-0 z-10 pb-2 border border-tertiary pb-safe">
+    <nav class="lg:hidden bg-surface md:bg-container shrink-0 z-10 pb-2 border-t border-tertiary pb-safe">
       <ul class="flex items-center justify-around gap-1">
         <li>
           <%= render "layouts/sidebar/nav_item", name: "Home", path: root_path, icon_key: "pie-chart" %>
diff --git a/app/views/layouts/shared/_htmldoc.html.erb b/app/views/layouts/shared/_htmldoc.html.erb
index 6e213a25..40f99179 100644
--- a/app/views/layouts/shared/_htmldoc.html.erb
+++ b/app/views/layouts/shared/_htmldoc.html.erb
@@ -6,17 +6,18 @@
   </head>
 
   <body class="h-screen overflow-hidden lg:overflow-auto antialiased h-screen-safe ">
-    <div class="fixed z-50 top-6 md:top-auto md:bottom-6 md:left-24 w-full md:w-80 mx-auto md:mx-0 md:right-auto mt-safe">
+    <div class="fixed z-50 top-6 md:top-4 md:left-1/2 -translate-x-1/2 w-full md:w-80 mx-auto md:mx-0 md:right-auto mt-safe">
       <div id="notification-tray" class="space-y-1 w-full">
         <%= render_flash_notifications %>
 
+        <div id="cta"></div>
+
         <% if Current.family&.syncing? %>
-          <%= render "shared/syncing_notice" %>
+          <% render "shared/notifications/loading", id: "syncing-notice", message: "Syncing accounts data..." %>
         <% end %>
       </div>
     </div>
 
-    <%= family_notifications_stream %>
     <%= family_stream %>
 
     <%= turbo_frame_tag "modal" %>
diff --git a/app/views/layouts/shared/_notifications.html.erb b/app/views/layouts/shared/_notifications.html.erb
deleted file mode 100644
index 4d55e272..00000000
--- a/app/views/layouts/shared/_notifications.html.erb
+++ /dev/null
@@ -1,12 +0,0 @@
-<div class="fixed z-50 bottom-6 left-6">
-  <div id="notification-tray" class="space-y-1">
-    <%= render_flash_notifications %>
-
-    <% if Current.family&.syncing? %>
-      <%= render "shared/syncing_notice" %>
-    <% end %>
-  </div>
-</div>
-
-<%= family_notifications_stream %>
-<%= family_stream %>
diff --git a/app/views/layouts/sidebar/_nav_item.html.erb b/app/views/layouts/sidebar/_nav_item.html.erb
index 63c9191c..dd8661af 100644
--- a/app/views/layouts/sidebar/_nav_item.html.erb
+++ b/app/views/layouts/sidebar/_nav_item.html.erb
@@ -1,18 +1,16 @@
 <%# locals: (name:, path:, icon_key:, is_custom: false) %>
-<%= link_to path, class: "space-y-1 lg:py-1 group block relative" do %>
-  <% if page_active?(path) %>
-    <%= tag.div class: "w-4 h-1 bg-nav-indicator rounded-bl-sm rounded-br-sm absolute top-0 left-1/2 -translate-x-1/2 lg:hidden" %>
-  <% end %>
+<%= link_to path, class: "space-y-1 group block relative pb-1" do %>
   <div class="grow flex flex-col lg:flex-row gap-1 items-center">
     <%= tag.div class: class_names("w-4 h-1 lg:w-1 lg:h-4 rounded-bl-sm rounded-br-sm lg:rounded-tr-sm lg:rounded-br-sm lg:rounded-bl-none", "bg-nav-indicator" => page_active?(path)) %>
 
     <% icon_color = page_active?(path) ? "current" : "gray" %>
+
     <%= tag.div class: class_names("w-8 h-8 flex items-center justify-center mx-auto rounded-lg", page_active?(path) ? "bg-container shadow-xs text-primary" : "group-hover:bg-container-hover text-secondary") do %>
       <%= is_custom ? icon_custom(icon_key, color: icon_color) : icon(icon_key, color: icon_color) %>
     <% end %>
   </div>
 
-  <div class="grow flex justify-center">
+  <div class="grow flex justify-center lg:pl-2">
     <%= tag.p class: class_names("font-medium text-[11px]", page_active?(path) ? "text-primary" : "text-secondary") do %>
       <%= name %>
     <% end %>
diff --git a/app/views/messages/_chat_form.html.erb b/app/views/messages/_chat_form.html.erb
index 7e5157fa..f2a36b63 100644
--- a/app/views/messages/_chat_form.html.erb
+++ b/app/views/messages/_chat_form.html.erb
@@ -4,25 +4,32 @@
   <% model = chat && chat.persisted? ? [chat, Message.new] : Chat.new %>
 
   <%= form_with model: model,
-                class: "flex items-center gap-2 bg-container p-2 rounded-full shadow-sm border border-gray-100 h-11",
+                class: "flex lg:flex-col gap-2 bg-container px-2 py-1.5 rounded-full lg:rounded-lg shadow-border-xs",
                 data: { chat_target: "form" } do |f| %>
 
     <%# In the future, this will be a dropdown with different AI models %>
     <%= f.hidden_field :ai_model, value: "gpt-4o" %>
-    
-    <button type="button" class="flex-shrink-0 text-secondary p-1">
-      <%= lucide_icon("plus", class: "w-5 h-5") %>
-    </button>
 
     <%= f.text_area :content, placeholder: "Ask anything ...", value: message_hint,
-                  class: "w-full border-0 focus:ring-0 text-sm resize-none bg-transparent py-0",
+                  class: "w-full border-0 focus:ring-0 text-sm resize-none px-1 bg-transparent",
                   data: { chat_target: "input", action: "input->chat#autoResize keydown->chat#handleInputKeyDown" },
                   rows: 1 %>
 
-    <button type="submit" class="flex-shrink-0 text-secondary bg-gray-50 rounded-full p-2">
-      <%= lucide_icon("arrow-up", class: "w-4 h-4") %>
-    </button>
+    <div class="flex items-center justify-between gap-1">
+      <div class="items-center gap-1 hidden lg:flex">
+        <%# These are disabled for now, but in the future, will all open specific menus with their own context and search %>
+        <% ["plus", "command", "at-sign", "mouse-pointer-click"].each do |icon| %>
+          <button type="button" title="Coming soon" class="cursor-not-allowed w-8 h-8 flex justify-center items-center hover:bg-surface-hover rounded-lg">
+            <%= icon(icon, color: "gray") %>
+          </button>
+        <% end %>
+      </div>
+
+      <button type="submit" class="w-8 h-8 flex justify-center items-center text-secondary hover:bg-surface-hover cursor-pointer rounded-lg">
+        <%= icon("arrow-up") %>
+      </button>
+    </div>
   <% end %>
 
-  <p class="text-xs text-secondary mt-1">AI responses are informational only and are not financial advice.</p>
-</div>
+  <p class="text-xs text-secondary">AI responses are informational only and are not financial advice.</p>
+</div>
\ No newline at end of file
diff --git a/app/views/rule/actions/_action.html.erb b/app/views/rule/actions/_action.html.erb
new file mode 100644
index 00000000..359eec33
--- /dev/null
+++ b/app/views/rule/actions/_action.html.erb
@@ -0,0 +1,27 @@
+<%# locals: (form:) %>
+
+<% action = form.object %>
+<% rule = action.rule %>
+<% needs_value = action.executor.type == "select" %>
+
+<li data-controller="rule--actions" data-rule--actions-action-executors-value="<%= rule.action_executors.to_json %>" class="flex items-center gap-3">
+  <%= form.hidden_field :_destroy, value: false, data: { rule__actions_target: "destroyField" } %>
+
+  <div class="grow flex gap-2 items-center h-full">
+    <div class="grow">
+      <%= form.select :action_type, rule.action_executors.map { |executor| [ executor.label, executor.key ] }, {}, data: { action: "rule--actions#handleActionTypeChange" } %>
+    </div>
+
+    <%= tag.div class: class_names("min-w-1/2 flex items-center gap-2", "hidden" => !needs_value), 
+                data: { rule__actions_target: "actionValue" } do %>
+      <span class="font-medium uppercase text-xs">to</span>
+      <%= form.select :value, action.options || [], {}, disabled: !needs_value %>
+    <% end %>
+  </div>
+
+  <button type="button"
+          data-action="rule--actions#remove"
+          data-rule--actions-destroy-param="<%= action.persisted? %>">
+    <%= icon("trash-2", color: "gray", size: "sm") %>
+  </button>
+</li>
diff --git a/app/views/rule/conditions/_condition.html.erb b/app/views/rule/conditions/_condition.html.erb
new file mode 100644
index 00000000..972c3d1d
--- /dev/null
+++ b/app/views/rule/conditions/_condition.html.erb
@@ -0,0 +1,40 @@
+<%# locals: (form:, show_prefix: true) %>
+
+<% condition = form.object %>
+<% rule = condition.rule %>
+
+<li data-controller="rule--conditions" data-rule--conditions-condition-filters-value="<%= rule.condition_filters.to_json %>" class="flex items-center gap-3">
+  <% if form.index.to_i > 0 && show_prefix %>
+    <div class="pl-4">
+      <span class="font-medium uppercase text-xs">and</span>
+    </div>
+  <% end %>
+
+  <div class="grow flex gap-2 items-center h-full">
+    <%= form.hidden_field :_destroy, value: false, data: { rule__conditions_target: "destroyField" } %>
+
+    <div class="w-2/5 shrink-0">
+      <%= form.select :condition_type, rule.condition_filters.map { |filter| [ filter.label, filter.key ] }, {}, data: { action: "rule--conditions#handleConditionTypeChange" } %>
+    </div>
+
+    <%= form.select :operator, condition.operators, { container_class: "w-fit min-w-36" }, data: { rule__conditions_target: "operatorSelect" } %>
+
+    <div data-rule--conditions-target="filterValue" class="grow">
+      <% if condition.filter.type == "select" %>
+        <%= form.select :value, condition.options, {} %>
+      <% else %>
+        <% if condition.filter.type == "number" %>
+          <%= form.number_field :value, placeholder: "10", step: 0.01 %>
+        <% else %>
+          <%= form.text_field :value, placeholder: "Enter a value" %>
+        <% end %>
+      <% end %>
+    </div>
+  </div>
+
+  <button type="button"
+          data-action="rule--conditions#remove"
+          data-rule--conditions-destroy-param="<%= condition.persisted? %>">
+    <%= icon("trash-2", color: "gray", size: "sm") %>
+  </button>
+</li>
diff --git a/app/views/rule/conditions/_condition_group.html.erb b/app/views/rule/conditions/_condition_group.html.erb
new file mode 100644
index 00000000..3da50432
--- /dev/null
+++ b/app/views/rule/conditions/_condition_group.html.erb
@@ -0,0 +1,44 @@
+<%# locals: (form:) %>
+
+<% condition = form.object %>
+<% rule = condition.rule %>
+
+<li data-controller="rule--conditions element-removal" class="border border-alpha-black-100 rounded-md p-4 space-y-3">
+
+  <%= form.hidden_field :condition_type, value: "compound" %>
+
+  <div class="flex items-center justify-between gap-2">
+    <div class="flex items-center gap-2">
+      <% unless form.index == 0 %>
+        <div class="pl-2">
+          <span class="font-medium uppercase text-xs">and</span>
+        </div>
+      <% end %>
+      <p class="text-sm text-secondary">match</p>
+      <%= form.select :operator, [["all", "and"], ["any", "or"]], { container_class: "w-fit" }, data: { rules_target: "operatorField" } %>
+      <p class="text-sm text-secondary">of the following conditions</p>
+    </div>
+
+    <button type="button" data-action="element-removal#remove">
+      <%= icon("trash-2", color: "gray", size: "sm") %>
+    </button>
+  </div>
+
+  <%# Sub-condition template, used by Stimulus controller to add new sub-conditions dynamically %>
+  <template data-rule--conditions-target="subConditionTemplate">
+    <%= form.fields_for :sub_conditions, Rule::Condition.new(parent: condition, condition_type: rule.condition_filters.first.key), child_index: "IDX_PLACEHOLDER" do |scf| %>
+      <%= render "rule/conditions/condition", form: scf %>
+    <% end %>
+  </template>
+
+  <ul data-rule--conditions-target="subConditionsList" class="space-y-3">
+    <%= form.fields_for :sub_conditions do |scf| %>
+      <%= render "rule/conditions/condition", form: scf, show_prefix: false %>
+    <% end %>
+  </ul>
+
+  <button type="button" class="btn btn--ghost" data-action="rule--conditions#addSubCondition">
+    <%= icon("plus", color: "gray", size: "sm") %>
+    <span>Add condition</span>
+  </button>
+</li>
diff --git a/app/views/rules/_category_rule_cta.html.erb b/app/views/rules/_category_rule_cta.html.erb
new file mode 100644
index 00000000..2035a4f0
--- /dev/null
+++ b/app/views/rules/_category_rule_cta.html.erb
@@ -0,0 +1,20 @@
+<%# locals: (cta:) %>
+
+<% message = "Updated to #{cta[:category_name]}" %>
+<% description = "You can create a rule to automatically categorize transactions like this one" %>
+
+<%= render "shared/notifications/cta", message: message, description: description do %>
+  <%= form_with model: Current.user, url: rule_prompt_settings_user_path(Current.user), method: :patch do |f| %>
+    <div class="flex gap-2 items-center mb-3 -mt-1">
+      <%= f.check_box :rule_prompts_disabled, class: "checkbox checkbox--light" %>
+      <%= f.label :rule_prompts_disabled, "Don't show this again", class: "text-xs text-secondary" %>
+    </div>
+
+    <%= f.hidden_field :rule_prompt_dismissed_at, value: Time.current %>
+
+    <%= tag.div class:"flex gap-2 justify-end" do %>
+      <%= f.submit "Dismiss", class: "btn btn--secondary" %>
+      <%= tag.a "Create rule", href: new_rule_path(resource_type: "transaction", action_type: "set_transaction_category", action_value: cta[:category_id]), class: "btn btn--primary", data: { turbo_frame: "modal" } %>
+    <% end %>
+  <% end %>
+<% end %>
\ No newline at end of file
diff --git a/app/views/rules/_form.html.erb b/app/views/rules/_form.html.erb
new file mode 100644
index 00000000..ce0aaf3a
--- /dev/null
+++ b/app/views/rules/_form.html.erb
@@ -0,0 +1,98 @@
+<%# locals: (rule:) %>
+
+<%= styled_form_with model: rule, class: "space-y-4 w-[550px]",
+                     data: { controller: "rules", rule_registry_value: rule.registry.to_json } do |f| %>
+
+  <%= f.hidden_field :resource_type, value: rule.resource_type %>
+
+  <% if @rule.errors.any? %>
+    <%= render "shared/form_errors", model: @rule %>
+  <% end %>
+
+  <section class="space-y-4">
+    <h3 class="text-sm font-medium">If <%= rule.resource_type %></h3>
+
+    <%# Condition template, used by Stimulus controller to add new conditions dynamically %>
+    <template data-rules-target="conditionGroupTemplate">
+      <%= f.fields_for :conditions, Rule::Condition.new(rule: rule, condition_type: "compound", operator: "and"), child_index: "IDX_PLACEHOLDER" do |cf| %>
+        <%= render "rule/conditions/condition_group", form: cf %>
+      <% end %>
+    </template>
+
+    <%# Condition template, used by Stimulus controller to add new conditions dynamically %>
+    <template data-rules-target="conditionTemplate">
+      <%= f.fields_for :conditions, Rule::Condition.new(rule: rule, condition_type: rule.condition_filters.first.key), child_index: "IDX_PLACEHOLDER" do |cf| %>
+        <%= render "rule/conditions/condition", form: cf %>
+      <% end %>
+    </template>
+
+    <ul data-rules-target="conditionsList" class="space-y-3 mb-4">
+      <%= f.fields_for :conditions do |cf| %>
+        <% if cf.object.compound? %>
+          <%= render "rule/conditions/condition_group", form: cf %>
+        <% else %>
+          <%= render "rule/conditions/condition", form: cf %>
+        <% end %>
+      <% end %>
+    </ul>
+
+    <div class="flex items-center gap-2">
+      <button type="button" data-action="rules#addCondition" class="btn btn--ghost">
+        <%= icon("plus") %>
+        <span>Add condition</span>
+      </button>
+
+      <button type="button" data-action="rules#addConditionGroup" class="btn btn--ghost">
+        <%= icon("boxes") %>
+        <span>Add condition group</span>
+      </button>
+    </div>
+  </section>
+
+  <section class="space-y-4">
+    <h3 class="text-sm font-medium">Then</h3>
+
+    <%# Action template, used by Stimulus controller to add new actions dynamically %>
+    <template data-rules-target="actionTemplate">
+      <%= f.fields_for :actions, Rule::Action.new(rule: rule, action_type: rule.action_executors.first.key), child_index: "IDX_PLACEHOLDER" do |af| %>
+        <%= render "rule/actions/action", form: af %>
+      <% end %>
+    </template>
+
+    <ul data-rules-target="actionsList" class="space-y-3">
+      <%= f.fields_for :actions do |af| %>
+        <%= render "rule/actions/action", form: af %>
+      <% end %>
+    </ul>
+
+    <button
+        type="button"
+        data-action="rules#addAction"
+        class="btn btn--ghost">
+      <%= icon("plus") %>
+      <span>Add action</span>
+    </button>
+  </section>
+
+  <section class="space-y-4">
+    <h3 class="text-sm font-medium">Apply this</h3>
+
+    <div class="space-y-2">
+      <div class="flex items-center gap-2">
+        <%= f.radio_button :effective_date_enabled, false, checked: rule.effective_date.nil?, data: { action: "rules#clearEffectiveDate" } %>
+        <%= f.label :effective_date_enabled_false, "To all past and future #{rule.resource_type}s", class: "text-sm" %>
+      </div>
+
+      <div class="flex items-center gap-2">
+        <div class="flex items-center gap-2">
+          <%= f.radio_button :effective_date_enabled, true, checked: rule.effective_date.present? %>
+          <%= f.label :effective_date_enabled_true, "Starting from", class: "text-sm" %>
+        </div>
+
+        <%= f.date_field :effective_date, container_class: "w-fit", data: { rules_target: "effectiveDateInput" } %>
+      </div>
+    </div>
+  </section>
+
+  <%= f.submit %>
+<% end %>
diff --git a/app/views/rules/_rule.html.erb b/app/views/rules/_rule.html.erb
new file mode 100644
index 00000000..91f4bd92
--- /dev/null
+++ b/app/views/rules/_rule.html.erb
@@ -0,0 +1,41 @@
+<%# locals: (rule:) %>
+
+<div class="flex justify-between items-center gap-4 bg-white shadow-border-xs rounded-md p-4">
+  <div class="text-sm space-y-1.5">
+    <p class="flex items-center flex-wrap gap-1.5">
+      <span class="px-2 py-1 border border-alpha-black-200 rounded-full">
+        <%= rule.actions.first.executor.label %>
+      </span>
+
+      <% if rule.actions.count > 1 %>
+        and <%= rule.actions.count - 1 %> more <%= rule.actions.count - 1 == 1 ? "action" : "actions" %>
+      <% end %>
+    </p>
+
+    <p class="flex items-center flex-wrap gap-1.5">
+      <% if rule.effective_date.nil? %>
+        To all past and future <%= rule.resource_type.pluralize %>
+      <% else %>
+        To all <%= rule.resource_type.pluralize %> on or after <%= rule.effective_date %>
+      <% end %>
+    </p>
+  </div>
+
+  <div class="flex items-center gap-4">
+    <%= render "shared/toggle_form", model: rule, attribute: :active %>
+
+    <%= contextual_menu icon: "more-vertical", id: "chat-menu" do %>
+      <%= contextual_menu_item "Edit", url: edit_rule_path(rule), icon: "pencil", turbo_frame: "modal" %>
+
+      <%= contextual_menu_item "Re-apply rule", url: confirm_rule_path(rule), turbo_frame: "modal", icon: "refresh-cw" %>
+
+      <% turbo_confirm = {
+        title: "Delete rule",
+        body: "Are you sure you want to delete this rule? Data affected by this rule will no longer be automatically updated. This action cannot be undone.",
+        accept: "Delete rule",
+      } %>
+
+      <%= contextual_menu_destructive_item "Delete", rule_path(rule), turbo_confirm: turbo_confirm %>
+    <% end %>
+  </div>
+</div>
diff --git a/app/views/rules/confirm.html.erb b/app/views/rules/confirm.html.erb
new file mode 100644
index 00000000..90d36e6f
--- /dev/null
+++ b/app/views/rules/confirm.html.erb
@@ -0,0 +1,20 @@
+<%= modal(reload_on_close: true) do %>
+  <div class="space-y-4 p-4 max-w-[400px]">
+    <div>
+      <div class="flex justify-between mb-2 gap-4">
+        <h3 class="font-medium text-md">Confirm changes</h3>
+        <button data-action="mousedown->modal#close">
+          <%= lucide_icon("x", class: "w-5 h-5 shrink-0 text-secondary") %>
+        </button>
+      </div>
+      <div class="text-secondary text-sm">
+        <p>
+          You are about to apply this rule to 
+          <span class="text-primary font-medium"><%= @rule.affected_resource_count %> <%= @rule.resource_type.pluralize %></span>
+          that meet the specified rule criteria.  Please confirm if you wish to proceed with this change.
+        </p>
+      </div>
+    </div>
+    <%= button_to "Confirm changes", apply_rule_path(@rule), class: "btn btn--primary w-full justify-center", data: { turbo_frame: "_top"} %>
+  </div>
+<% end %>
\ No newline at end of file
diff --git a/app/views/rules/edit.html.erb b/app/views/rules/edit.html.erb
new file mode 100644
index 00000000..e5693fa2
--- /dev/null
+++ b/app/views/rules/edit.html.erb
@@ -0,0 +1,5 @@
+<%= link_to "Back to rules", rules_path %>
+
+<%= modal_form_wrapper title: "Edit #{@rule.resource_type} rule" do %>
+  <%= render "rules/form", rule: @rule %>
+<% end %>
diff --git a/app/views/rules/index.html.erb b/app/views/rules/index.html.erb
new file mode 100644
index 00000000..3bf1ba6c
--- /dev/null
+++ b/app/views/rules/index.html.erb
@@ -0,0 +1,61 @@
+<header class="flex items-center justify-between">
+  <h1 class="text-primary text-xl font-medium">Rules</h1>
+
+  <% turbo_confirm = {
+    title: "Delete all rules",
+    body: "Are you sure you want to delete all rules? This action cannot be undone.",
+    accept: "Delete all rules",
+  } %>
+
+  <div class="flex items-center gap-2">
+    <% if @rules.any? %>
+      <%= contextual_menu do %>
+        <%= contextual_menu_destructive_item "Delete all rules", destroy_all_rules_path, turbo_confirm: turbo_confirm %>
+      <% end %>
+    <% end %>
+
+    <%= link_to new_rule_path(resource_type: "transaction"), class: "btn btn--primary flex items-center gap-1 justify-center", data: { turbo_frame: :modal } do %>
+      <%= lucide_icon "plus", class: "w-5 h-5" %>
+      <p>New rule</p>
+    <% end %>
+  </div>
+</header>
+
+<% if self_hosted? %>
+  <div class="flex items-center gap-2 mb-2 py-4">
+    <%= lucide_icon("circle-alert", class: "w-4 h-4 text-secondary") %>
+    <p class="text-sm text-secondary">
+      AI-enabled rule actions will cost money.  Be sure to filter as narrowly as possible to avoid unnecessary costs.
+    </p>
+  </div>
+<% end %>
+
+<div class="bg-white shadow-border-xs rounded-xl p-4">
+
+  <% if @rules.any? %>
+    <div class="rounded-xl bg-gray-25 space-y-1">
+      <div class="flex items-center gap-1.5 px-4 py-2 text-xs font-medium text-secondary uppercase">
+        <p>Rules</p>
+        <span class="text-subdued">&middot;</span>
+        <p><%= @rules.count %></p>
+      </div>
+
+      <div class="space-y-1 p-1">
+        <%= render @rules %>
+      </div>
+    </div>
+  <% else %>
+    <div class="flex justify-center items-center py-20">
+      <div class="text-center flex flex-col items-center max-w-[500px]">
+        <p class="text-sm text-primary font-medium mb-1">No rules yet</p>
+        <p class="text-sm text-secondary mb-4">Set up rules to perform actions to your transactions and other data on every account sync.</p>
+        <div class="flex items-center gap-2">
+          <%= link_to new_rule_path(resource_type: "transaction"), class: "btn btn--primary flex items-center gap-1", data: { turbo_frame: "modal" } do %>
+            <%= lucide_icon("plus", class: "w-5 h-5") %>
+            <span>New rule</span>
+          <% end %>
+        </div>
+      </div>
+    </div>
+  <% end %>
+</div>
diff --git a/app/views/rules/new.html.erb b/app/views/rules/new.html.erb
new file mode 100644
index 00000000..37205dd9
--- /dev/null
+++ b/app/views/rules/new.html.erb
@@ -0,0 +1,5 @@
+<%= link_to "Back to rules", rules_path %>
+
+<%= modal_form_wrapper title: "New #{@rule.resource_type} rule" do %>
+  <%= render "rules/form", rule: @rule %>
+<% end %>
diff --git a/app/views/settings/_settings_nav.html.erb b/app/views/settings/_settings_nav.html.erb
index 853b14b1..ea995458 100644
--- a/app/views/settings/_settings_nav.html.erb
+++ b/app/views/settings/_settings_nav.html.erb
@@ -61,7 +61,10 @@
           <%= render "settings/settings_nav_item", name: t(".categories_label"), path: categories_path, icon: "shapes" %>
         </li>
         <li>
-          <%= render "settings/settings_nav_item", name: t(".merchants_label"), path: merchants_path, icon: "store" %>
+          <%= render "settings/settings_nav_item", name: "Rules", path: rules_path, icon: "git-branch" %>
+        </li>
+        <li>
+          <%= render "settings/settings_nav_item", name: t(".merchants_label"), path: family_merchants_path, icon: "store" %>
         </li>
       </ul>
     </section>
@@ -87,72 +90,63 @@
     </section>
   </nav>
   <nav class="space-y-4 overflow-y-auto  md:hidden" id="mobile-settings-nav"  data-preserve-scroll data-controller="preserve-scroll">
-    
-      <ul class="flex space-y-1">
 
+    <ul class="flex space-y-1">
+
+      <li>
+        <%= render "settings/settings_nav_item", name: t(".profile_label"), path: settings_profile_path, icon: "circle-user" %>
+      </li>
+
+      <li>
+        <%= render "settings/settings_nav_item", name: t(".preferences_label"), path: settings_preferences_path, icon: "bolt" %>
+      </li>
+
+      <li>
+        <%= render "settings/settings_nav_item", name: t(".security_label"), path: settings_security_path, icon: "shield-check" %>
+      </li>
+
+      <% if self_hosted? %>
         <li>
-          <%= render "settings/settings_nav_item", name: t(".profile_label"), path: settings_profile_path, icon: "circle-user" %>
+          <%= render "settings/settings_nav_item", name: t(".self_hosting_label"), path: settings_hosting_path, icon: "database" %>
         </li>
-
+      <% end %>
+      <% unless self_hosted? %>
         <li>
-          <%= render "settings/settings_nav_item", name: t(".preferences_label"), path: settings_preferences_path, icon: "bolt" %>
-        </li>
-
-        <li>
-          <%= render "settings/settings_nav_item", name: t(".security_label"), path: settings_security_path, icon: "shield-check" %>
-        </li>
-
-        <% if self_hosted? %>
-          <li>
-            <%= render "settings/settings_nav_item", name: t(".self_hosting_label"), path: settings_hosting_path, icon: "database" %>
-          </li>
-        <% end %>
-        <% unless self_hosted? %>
-          <li>
-            <%= render "settings/settings_nav_item", name: t(".billing_label"), path: settings_billing_path, icon: "circle-dollar-sign" %>
-          </li>
-        <% end %>
-
-        <li>
-          <%= render "settings/settings_nav_item", name: t(".accounts_label"), path: accounts_path, icon: "layers" %>
-        </li>
-
-        <li>
-          <%= render "settings/settings_nav_item", name: t(".imports_label"), path: imports_path, icon: "download" %>
-        </li>
-
-        <li>
-          <%= render "settings/settings_nav_item", name: t(".tags_label"), path: tags_path, icon: "tags" %>
-        </li>
-        <li>
-          <%= render "settings/settings_nav_item", name: t(".categories_label"), path: categories_path, icon: "shapes" %>
-        </li>
-        <li>
-          <%= render "settings/settings_nav_item", name: t(".merchants_label"), path: merchants_path, icon: "store" %>
-        </li>
-
-
-
-
-
-        <li>
-          <%= render "settings/settings_nav_item", name: t(".whats_new_label"), path: changelog_path, icon: "box" %>
-        </li>
-        <li>
-          <%= render "settings/settings_nav_item", name: t(".feedback_label"), path: feedback_path, icon: "megaphone" %>
+          <%= render "settings/settings_nav_item", name: t(".billing_label"), path: settings_billing_path, icon: "circle-dollar-sign" %>
         </li>
+      <% end %>
 
+      <li>
+        <%= render "settings/settings_nav_item", name: t(".accounts_label"), path: accounts_path, icon: "layers" %>
+      </li>
 
+      <li>
+        <%= render "settings/settings_nav_item", name: t(".imports_label"), path: imports_path, icon: "download" %>
+      </li>
 
+      <li>
+        <%= render "settings/settings_nav_item", name: t(".tags_label"), path: tags_path, icon: "tags" %>
+      </li>
+      <li>
+        <%= render "settings/settings_nav_item", name: t(".categories_label"), path: categories_path, icon: "shapes" %>
+      </li>
+      <li>
+        <%= render "settings/settings_nav_item", name: t(".merchants_label"), path: family_merchants_path, icon: "store" %>
+      </li>
 
+      <li>
+        <%= render "settings/settings_nav_item", name: t(".whats_new_label"), path: changelog_path, icon: "box" %>
+      </li>
+      <li>
+        <%= render "settings/settings_nav_item", name: t(".feedback_label"), path: feedback_path, icon: "megaphone" %>
+      </li>
 
       <%= button_to session_path(Current.session), method: :delete, class: "flex items-center gap-2 btn btn--ghost text-destructive w-full" do %>
         <%= lucide_icon("log-out", class: "w-5 h-5 shrink-0") %>
         <span><%= t(".logout") %></span>
       <% end %>
 
-        </ul>
-
+    </ul>
 
   </nav>
 </div>
diff --git a/app/views/settings/preferences/_data_enrichment_settings.html.erb b/app/views/settings/preferences/_data_enrichment_settings.html.erb
deleted file mode 100644
index bce47776..00000000
--- a/app/views/settings/preferences/_data_enrichment_settings.html.erb
+++ /dev/null
@@ -1,24 +0,0 @@
-<%# locals: (user:) %>
-
-<div class="space-y-4">
-  <div class="flex items-center justify-between">
-    <div class="space-y-1">
-      <p class="text-sm"><%= t(".title") %></p>
-      <p class="text-secondary text-sm"><%= t(".description") %></p>
-      <% if self_hosted? %>
-        <p class="text-xs italic text-secondary"><%= t(".self_host_disclaimer") %></p>
-      <% end %>
-    </div>
-
-    <%= styled_form_with model: user,
-                         data: { controller: "auto-submit-form", "auto-submit-form-trigger-event-value": "blur" } do |form| %>
-      <div class="relative inline-block select-none">
-        <%= form.hidden_field :redirect_to, value: "preferences" %>
-        <%= form.fields_for :family do |family_form| %>
-          <%= family_form.check_box :data_enrichment_enabled, class: "sr-only peer", "data-auto-submit-form-target": "auto", "data-autosubmit-trigger-event": "input" %>
-          <%= family_form.label :data_enrichment_enabled, "&nbsp;".html_safe, class: "switch" %>
-        <% end %>
-      </div>
-    <% end %>
-  </div>
-</div>
diff --git a/app/views/settings/preferences/show.html.erb b/app/views/settings/preferences/show.html.erb
index e91567fd..99857aba 100644
--- a/app/views/settings/preferences/show.html.erb
+++ b/app/views/settings/preferences/show.html.erb
@@ -41,10 +41,6 @@
   </div>
 <% end %>
 
-<%= settings_section title: t(".data"), subtitle: t(".data_subtitle") do %>
-  <%= render "settings/preferences/data_enrichment_settings", user: @user %>
-<% end %>
-
 <%= settings_section title: t(".theme_title"), subtitle: t(".theme_subtitle") do %>
   <div>
     <%= styled_form_with model: @user, class: "flex flex-col md:flex-row justify-between items-center gap-4", data: { controller: "auto-submit-form" } do |form| %>
diff --git a/app/views/shared/_confirm_modal.html.erb b/app/views/shared/_confirm_modal.html.erb
index eb1ca925..52410d14 100644
--- a/app/views/shared/_confirm_modal.html.erb
+++ b/app/views/shared/_confirm_modal.html.erb
@@ -11,7 +11,6 @@
         <%= t(".body_html") %>
       </div>
     </div>
-    <button id="turbo-confirm-accept" class="w-full text-red-600 rounded-xl text-center p-[10px] border mb-2" value="confirm"><%= t(".accept") %></button>
-    <button class="w-full rounded-xl text-center p-[10px] border" value="cancel"><%= t(".cancel") %></button>
+    <button id="turbo-confirm-accept" class="btn btn--outline-destructive justify-center w-full mb-2" value="confirm"><%= t(".accept") %></button>
   </form>
 </dialog>
diff --git a/app/views/shared/_modal.html.erb b/app/views/shared/_modal.html.erb
index ce7c0394..3fdcb70a 100644
--- a/app/views/shared/_modal.html.erb
+++ b/app/views/shared/_modal.html.erb
@@ -1,8 +1,19 @@
-<%# locals: (content:, classes:) -%>
+<%# locals: (content:, reload_on_close:, overflow_visible: false) -%>
+
 <%= turbo_frame_tag "modal" do %>
-  <dialog class="md:m-auto bg-container shadow-border-xs rounded-none md:rounded-2xl max-w-screen max-h-screen md:max-w-max w-full h-full md:h-fit md:w-auto overflow-visible <%= classes %>" data-controller="modal" data-action="mousedown->modal#clickOutside">
+  <%= tag.dialog(
+    class: class_names(
+      "focus:outline-none md:m-auto bg-container rounded-none md:rounded-2xl max-w-screen max-h-screen md:max-w-max w-full h-full md:h-fit md:w-auto shadow-border-xs",
+      overflow_visible ? "overflow-visible" : "overflow-auto"
+    ),
+    data: {
+      controller: "modal",
+      action: "mousedown->modal#clickOutside",
+      modal_reload_on_close_value: reload_on_close
+    }
+  ) do %>
     <div class="flex flex-col h-full md:h-auto mt-safe">
       <%= content %>
     </div>
-  </dialog>
+  <% end %>
 <% end %>
diff --git a/app/views/shared/_modal_form.html.erb b/app/views/shared/_modal_form.html.erb
index 72c39039..cbf821c8 100644
--- a/app/views/shared/_modal_form.html.erb
+++ b/app/views/shared/_modal_form.html.erb
@@ -1,6 +1,6 @@
-<%# locals: (title:, content:, subtitle: nil) %>
+<%# locals: (title:, content:, subtitle: nil, overflow_visible: false) %>
 
-<%= modal do %>
+<%= modal overflow_visible: overflow_visible do %>
   <article class="mx-auto w-full p-4 space-y-4 md:min-w-[450px]">
     <div class="space-y-2">
       <header class="flex justify-between items-center">
diff --git a/app/views/shared/_notification.html.erb b/app/views/shared/_notification.html.erb
deleted file mode 100644
index 17393390..00000000
--- a/app/views/shared/_notification.html.erb
+++ /dev/null
@@ -1,42 +0,0 @@
-<%# locals: (message:, type: "notice", **_opts) %>
-
-<% type = type.to_sym %>
-<% action = "animationend->element-removal#remove" if type == :notice %>
-
-<%= tag.div class: "flex gap-3 rounded-lg border bg-container p-4 group max-w-80 shadow-xs border-alpha-black-25 mx-auto md:mx-0",
-            data: {
-              controller: "element-removal",
-              action: action
-            } do %>
-
-  <div class="h-5 w-5 shrink-0 p-px text-white">
-    <% case type %>
-    <% when :notice %>
-      <div class="flex h-full items-center justify-center rounded-full bg-success">
-        <%= lucide_icon "check", class: "w-3 h-3" %>
-      </div>
-    <% when :alert %>
-      <div class="flex h-full items-center justify-center rounded-full bg-destructive">
-        <%= lucide_icon "x", class: "w-3 h-3" %>
-      </div>
-    <% end %>
-  </div>
-
-  <%= tag.p message, class: "text-primary text-sm font-medium" %>
-
-  <div class="ml-auto">
-    <% if type.to_sym == :notice %>
-      <div class="h-5 shrink-0">
-        <svg width="20" height="20" viewBox="0 0 20 20" fill="none" xmlns="http://www.w3.org/2000/svg" class="shrink-0">
-          <path d="M18 10C18 14.4183 14.4183 18 10 18C5.58172 18 2 14.4183 2 10C2 5.58172 5.58172 2 10 2C14.4183 2 18 5.58172 18 10ZM3.6 10C3.6 13.5346 6.46538 16.4 10 16.4C13.5346 16.4 16.4 13.5346 16.4 10C16.4 6.46538 13.5346 3.6 10 3.6C6.46538 3.6 3.6 6.46538 3.6 10Z" fill="#E5E5E5" />
-          <circle class="origin-center -rotate-90 animate-[stroke-fill_2.2s_300ms_forwards]" stroke="#141414" stroke-opacity="0.4" r="7.2" cx="10" cy="10" stroke-dasharray="43.9822971503" stroke-dashoffset="43.9822971503" />
-        </svg>
-        <div class="absolute -top-2 -right-2">
-          <%= lucide_icon "x", class: "w-5 h-5 p-0.5 hidden group-hover:inline-block border border-alpha-black-50 border-solid rounded-lg bg-container text-subdued cursor-pointer", data: { action: "click->element-removal#remove" } %>
-        </div>
-      </div>
-    <% elsif type.to_sym == :alert %>
-      <%= lucide_icon "x", data: { action: "click->element-removal#remove" }, class: "w-5 h-5 text-secondary hover:text-gray-600 cursor-pointer" %>
-    <% end %>
-  </div>
-<% end %>
diff --git a/app/views/shared/_syncing_notice.html.erb b/app/views/shared/_syncing_notice.html.erb
deleted file mode 100644
index 07e163bf..00000000
--- a/app/views/shared/_syncing_notice.html.erb
+++ /dev/null
@@ -1,7 +0,0 @@
-<%= tag.div id: "syncing-notice", class: "flex gap-3 rounded-lg border bg-container p-4 group w-full shadow-xs border-alpha-black-25" do %>
-  <div class="h-5 w-5 shrink-0 p-px text-white">
-    <%= lucide_icon "loader", class: "w-5 h-5 text-secondary animate-pulse" %>
-  </div>
-
-  <%= tag.p t(".syncing"), class: "text-primary text-sm font-medium" %>
-<% end %>
diff --git a/app/views/shared/_toggle_form.html.erb b/app/views/shared/_toggle_form.html.erb
new file mode 100644
index 00000000..a5d1ed25
--- /dev/null
+++ b/app/views/shared/_toggle_form.html.erb
@@ -0,0 +1,11 @@
+<%# locals: (model:, attribute:, turbo_frame: nil) %>
+
+<%= form_with model: model,
+              namespace: model.id,
+              class: "flex items-center",
+              data: { controller: "auto-submit-form", turbo_frame: turbo_frame } do |form| %>
+  <div class="relative inline-block select-none">
+    <%= form.check_box attribute, { class: "sr-only peer", data: { "auto-submit-form-target": "auto" } } %>
+    <%= form.label attribute, "&nbsp;".html_safe, class: "switch" %>
+  </div>
+<% end %>
diff --git a/app/views/shared/notifications/_alert.html.erb b/app/views/shared/notifications/_alert.html.erb
new file mode 100644
index 00000000..3b513aa6
--- /dev/null
+++ b/app/views/shared/notifications/_alert.html.erb
@@ -0,0 +1,16 @@
+<%# locals: (message:) %>
+
+<%= tag.div class: "flex gap-3 rounded-lg bg-white p-4 group max-w-80 shadow-border-lg",
+            data: { controller: "element-removal" } do %>
+  <div class="h-5 w-5 shrink-0 p-px text-white">
+    <div class="flex h-full items-center justify-center rounded-full bg-destructive">
+      <%= lucide_icon "x", class: "w-3 h-3" %>
+    </div>
+  </div>
+
+  <%= tag.p message, class: "text-primary text-sm font-medium" %>
+
+  <div class="ml-auto">
+    <%= lucide_icon "x", data: { action: "click->element-removal#remove" }, class: "w-5 h-5 text-secondary hover:text-gray-600 cursor-pointer" %>
+  </div>
+<% end %>
diff --git a/app/views/shared/notifications/_cta.html.erb b/app/views/shared/notifications/_cta.html.erb
new file mode 100644
index 00000000..57e408c6
--- /dev/null
+++ b/app/views/shared/notifications/_cta.html.erb
@@ -0,0 +1,20 @@
+<%# locals: (message:, description:) %>
+
+<div id="cta">
+  <%= tag.div class: "relative flex gap-3 rounded-lg bg-white p-4 group max-w-80 shadow-border-xs", data: { controller: "element-removal" } do %>
+    <div class="h-5 w-5 shrink-0 p-px text-white">
+      <div class="flex h-full items-center justify-center rounded-full bg-success">
+        <%= lucide_icon "check", class: "w-3 h-3" %>
+      </div>
+    </div>
+
+    <div class="space-y-4">
+      <div class="space-y-1">
+        <%= tag.p message, class: "text-primary text-sm font-medium" %>
+        <%= tag.p description, class: "text-secondary text-sm" %>
+      </div>
+
+      <%= yield %>
+    </div>
+  <% end %>
+</div>
diff --git a/app/views/shared/notifications/_loading.html.erb b/app/views/shared/notifications/_loading.html.erb
new file mode 100644
index 00000000..e654171a
--- /dev/null
+++ b/app/views/shared/notifications/_loading.html.erb
@@ -0,0 +1,9 @@
+<%# locals: (message:, id: nil) %>
+
+<%= tag.div id: id, class: "flex gap-3 rounded-lg bg-white p-4 group w-full shadow-border-xs" do %>
+  <div class="h-5 w-5 shrink-0 p-px text-white">
+    <%= lucide_icon "loader", class: "w-5 h-5 text-secondary animate-pulse" %>
+  </div>
+
+  <%= tag.p message, class: "text-primary text-sm font-medium" %>
+<% end %>
diff --git a/app/views/shared/notifications/_notice.html.erb b/app/views/shared/notifications/_notice.html.erb
new file mode 100644
index 00000000..fcb62e09
--- /dev/null
+++ b/app/views/shared/notifications/_notice.html.erb
@@ -0,0 +1,48 @@
+<%# locals: (message:, description: nil, cta: nil) %>
+
+<%= tag.div class: "relative flex gap-3 rounded-lg bg-white p-4 group max-w-80 shadow-border-xs",
+            data: {
+              controller: "element-removal",
+              action: "animationend->element-removal#remove"
+            } do %>
+
+  <div class="h-5 w-5 shrink-0 p-px text-white">
+    <div class="flex h-full items-center justify-center rounded-full bg-success">
+      <%= lucide_icon "check", class: "w-3 h-3" %>
+    </div>
+  </div>
+
+  <div class="space-y-4">
+    <div class="space-y-1">
+      <%= tag.p message, class: "text-primary text-sm font-medium" %>
+
+      <% if description %>
+        <%= tag.p description, class: "text-secondary text-sm" %>
+      <% end %>
+    </div>
+
+    <% if cta %>
+      <%= tag.div class:"flex gap-2 justify-end" do %>
+        <%= tag.button cta[:decline][:label], class: "btn btn--secondary", data: { action: "click->element-removal#remove" } %>
+        <%= tag.a cta[:accept][:label], href: cta[:accept][:href], class: "btn btn--primary" %>
+      <% end %>
+    <% end %>
+  </div>
+
+  <div class="ml-auto">
+    <div class="h-5 shrink-0">
+      <% unless cta %>
+        <svg width="20" height="20" viewBox="0 0 20 20" fill="none" xmlns="http://www.w3.org/2000/svg" class="shrink-0">
+          <path d="M18 10C18 14.4183 14.4183 18 10 18C5.58172 18 2 14.4183 2 10C2 5.58172 5.58172 2 10 2C14.4183 2 18 5.58172 18 10ZM3.6 10C3.6 13.5346 6.46538 16.4 10 16.4C13.5346 16.4 16.4 13.5346 16.4 10C16.4 6.46538 13.5346 3.6 10 3.6C6.46538 3.6 3.6 6.46538 3.6 10Z" fill="#E5E5E5" />
+          <circle class="origin-center -rotate-90 animate-stroke-fill" stroke="#141414" stroke-opacity="0.4" r="7.2" cx="10" cy="10" stroke-dasharray="43.9822971503" stroke-dashoffset="43.9822971503" />
+        </svg>
+      <% end %>
+    </div>
+  </div>
+
+  <% unless cta %>
+    <div class="absolute -top-2 -right-2">
+      <%= lucide_icon "x", class: "w-5 h-5 p-0.5 hidden group-hover:inline-block border border-alpha-black-50 border-solid rounded-lg bg-white text-subdued cursor-pointer", data: { action: "click->element-removal#remove" } %>
+    </div>
+  <% end %>
+<% end %>
diff --git a/app/views/trades/_trade.html.erb b/app/views/trades/_trade.html.erb
index 9d8bed5f..eb558dd3 100644
--- a/app/views/trades/_trade.html.erb
+++ b/app/views/trades/_trade.html.erb
@@ -13,11 +13,11 @@
         <div class="max-w-full">
           <%= tag.div class: ["flex items-center gap-2"] do %>
             <div class="flex h-8 w-8 shrink-0 items-center justify-center rounded-full bg-gray-600/5 text-gray-600">
-              <%= entry.display_name.first.upcase %>
+              <%= entry.name.first.upcase %>
             </div>
 
             <div class="truncate">
-              <%= link_to entry.display_name,
+              <%= link_to entry.name,
                         entry_path(entry),
                         data: { turbo_frame: "drawer", turbo_prefetch: false },
                         class: "hover:underline hover:text-gray-800" %>
diff --git a/app/views/trades/show.html.erb b/app/views/trades/show.html.erb
index 38cb890b..565f8c8b 100644
--- a/app/views/trades/show.html.erb
+++ b/app/views/trades/show.html.erb
@@ -1,4 +1,4 @@
-<%= drawer(reload_on_close: true) do %>
+<%= drawer do %>
   <%= render "trades/header", entry: @entry %>
 
   <% trade = @entry.trade %>
diff --git a/app/views/transactions/_header.html.erb b/app/views/transactions/_header.html.erb
index 5b3e75b8..410429ee 100644
--- a/app/views/transactions/_header.html.erb
+++ b/app/views/transactions/_header.html.erb
@@ -20,4 +20,4 @@
   <span class="text-sm text-secondary">
     <%= I18n.l(entry.date, format: :long) %>
   </span>
-<% end %>
+<% end %>
\ No newline at end of file
diff --git a/app/views/transactions/_transaction.html.erb b/app/views/transactions/_transaction.html.erb
index d2fb2423..dde46135 100644
--- a/app/views/transactions/_transaction.html.erb
+++ b/app/views/transactions/_transaction.html.erb
@@ -21,13 +21,13 @@
 
         <div class="max-w-full">
           <%= content_tag :div, class: ["flex items-center gap-2"] do %>
-            <% if transaction.merchant&.icon_url %>
-              <%= image_tag transaction.merchant.icon_url,
+            <% if transaction.merchant&.logo_url.present? %>
+              <%= image_tag transaction.merchant.logo_url,
                   class: "w-6 h-6 rounded-full",
                   loading: "lazy" %>
             <% else %>
               <%= render "shared/circle_logo",
-                  name: entry.display_name,
+                  name: entry.name,
                   size: "sm" %>
             <% end %>
 
@@ -35,7 +35,7 @@
               <div class="space-y-0.5">
                 <div class="flex items-center gap-1">
                   <%= link_to(
-                        transaction.transfer? ? transaction.transfer.name : entry.display_name,
+                        transaction.transfer? ? transaction.transfer.name : entry.name,
                         transaction.transfer? ? transfer_path(transaction.transfer) : entry_path(entry),
                         data: {
                           turbo_frame: "drawer",
diff --git a/app/views/transactions/index.html.erb b/app/views/transactions/index.html.erb
index c0f32270..7ed329aa 100644
--- a/app/views/transactions/index.html.erb
+++ b/app/views/transactions/index.html.erb
@@ -4,9 +4,14 @@
     <div class="flex items-center gap-5">
       <div class="flex items-center gap-2">
         <%= contextual_menu do %>
+          <% if Rails.env.development? %>
+            <%= button_to "Dev only: Sync all", sync_all_accounts_path, class: "btn btn--ghost w-full" %>
+          <% end %>
+          <%= contextual_menu_item "New rule", url: new_rule_path(resource_type: "transaction"), icon: "plus", turbo_frame: :modal %>
+          <%= contextual_menu_item "Edit rules", url: rules_path, icon: "git-branch", turbo_frame: :_top %>
           <%= contextual_menu_modal_action_item t(".edit_categories"), categories_path, icon: "shapes", turbo_frame: :_top %>
           <%= contextual_menu_modal_action_item t(".edit_tags"), tags_path, icon: "tags", turbo_frame: :_top %>
-          <%= contextual_menu_modal_action_item t(".edit_merchants"), merchants_path, icon: "store", turbo_frame: :_top %>
+          <%= contextual_menu_modal_action_item t(".edit_merchants"), family_merchants_path, icon: "store", turbo_frame: :_top %>
           <%= contextual_menu_modal_action_item t(".edit_imports"), imports_path, icon: "hard-drive-upload", turbo_frame: :_top %>
           <%= contextual_menu_modal_action_item t(".import"), new_import_path, icon: "download", turbo_frame: "modal", class_name: "md:!hidden" %>
         <% end %>
diff --git a/app/views/transactions/searches/filters/_merchant_filter.html.erb b/app/views/transactions/searches/filters/_merchant_filter.html.erb
index 9910134c..3fb044b5 100644
--- a/app/views/transactions/searches/filters/_merchant_filter.html.erb
+++ b/app/views/transactions/searches/filters/_merchant_filter.html.erb
@@ -5,7 +5,7 @@
     <%= lucide_icon("search", class: "w-5 h-5 text-secondary absolute inset-y-0 left-2 top-1/2 transform -translate-y-1/2") %>
   </div>
   <div class="my-2" id="list" data-list-filter-target="list">
-    <% Current.family.merchants.alphabetically.each do |merchant| %>
+    <% Current.family.assigned_merchants.alphabetically.each do |merchant| %>
       <div class="filterable-item flex items-center gap-2 p-2" data-filter-name="<%= merchant.name %>">
         <%= form.check_box :merchants,
                            {
diff --git a/app/views/transactions/show.html.erb b/app/views/transactions/show.html.erb
index bf078dd3..7306ffc0 100644
--- a/app/views/transactions/show.html.erb
+++ b/app/views/transactions/show.html.erb
@@ -1,4 +1,4 @@
-<%= drawer(reload_on_close: true) do %>
+<%= drawer do %>
   <%= render "transactions/header", entry: @entry %>
 
   <div class="space-y-2">
@@ -10,7 +10,7 @@
               class: "space-y-2",
               data: { controller: "auto-submit-form" } do |f| %>
 
-          <%= f.text_field @entry.enriched_at.present? ? :enriched_name : :name,
+          <%= f.text_field :name,
                 label: t(".name_label"),
                 "data-auto-submit-form-target": "auto" %>
 
@@ -66,7 +66,7 @@
             <%= f.fields_for :entryable do |ef| %>
 
               <%= ef.collection_select :merchant_id,
-                      Current.family.merchants.alphabetically,
+                      Current.family.assigned_merchants.alphabetically,
                     :id, :name,
                     { include_blank: t(".none"),
                       label: t(".merchant_label"),
@@ -81,7 +81,7 @@
                       label:    t(".tags_label"),
                       container_class: "h-40"
                     },
-                  { "data-auto-submit-form-target": "auto" } %>
+                    { "data-auto-submit-form-target": "auto" } %>
             <% end %>
           <% end %>
 
diff --git a/app/views/valuations/_valuation.html.erb b/app/views/valuations/_valuation.html.erb
index 09694b34..1308a927 100644
--- a/app/views/valuations/_valuation.html.erb
+++ b/app/views/valuations/_valuation.html.erb
@@ -19,7 +19,7 @@
           <% end %>
 
           <div class="truncate text-primary">
-            <%= link_to entry.display_name,
+            <%= link_to entry.name,
                         entry_path(entry),
                         data: { turbo_frame: "drawer", turbo_prefetch: false },
                         class: "hover:underline hover:text-gray-800" %>
diff --git a/app/views/valuations/show.html.erb b/app/views/valuations/show.html.erb
index 94d01569..9a21b2e7 100644
--- a/app/views/valuations/show.html.erb
+++ b/app/views/valuations/show.html.erb
@@ -1,6 +1,6 @@
 <% entry, account = @entry, @entry.account %>
 
-<%= drawer(reload_on_close: true) do %>
+<%= drawer do %>
   <%= render "valuations/header", entry: %>
 
   <div class="space-y-2">
diff --git a/config/locales/views/categories/en.yml b/config/locales/views/categories/en.yml
index 1b3ee826..9f089fb7 100644
--- a/config/locales/views/categories/en.yml
+++ b/config/locales/views/categories/en.yml
@@ -15,7 +15,7 @@ en:
     form:
       placeholder: Category name
     index:
-      bootstrap: Use default categories
+      bootstrap: Use defaults (recommended)
       categories: Categories
       categories_expenses: Expense categories
       categories_incomes: Income categories
diff --git a/config/locales/views/merchants/en.yml b/config/locales/views/merchants/en.yml
index 3f31dd59..fab034ce 100644
--- a/config/locales/views/merchants/en.yml
+++ b/config/locales/views/merchants/en.yml
@@ -1,6 +1,6 @@
 ---
 en:
-  merchants:
+  family_merchants:
     create:
       error: 'Error creating merchant: %{error}'
       success: New merchant created successfully
diff --git a/config/locales/views/settings/en.yml b/config/locales/views/settings/en.yml
index c4b0f553..f5d01c0e 100644
--- a/config/locales/views/settings/en.yml
+++ b/config/locales/views/settings/en.yml
@@ -7,16 +7,9 @@ en:
         subscription_subtitle: Update your subscription and billing details
         subscription_title: Manage subscription
     preferences:
-      data_enrichment_settings:
-        description: Let Maybe auto-categorize, name, and add merchant data to your
-          transactions on each sync.  All enrichment is done in English.
-        self_host_disclaimer: This will incur Synth API credits.
-        title: Transaction enrichment (English only)
       show:
         country: Country
         currency: Currency
-        data: Data enrichment
-        data_subtitle: Enable data enrichment for your accounts
         date_format: Date format
         general_subtitle: Configure your preferences
         general_title: General
diff --git a/config/routes.rb b/config/routes.rb
index 35f1b2e3..501ffb99 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -32,6 +32,7 @@ Rails.application.routes.draw do
 
   resources :users, only: %i[update destroy] do
     delete :reset, on: :member
+    patch :rule_prompt_settings, on: :member
   end
 
   resource :onboarding, only: :show do
@@ -67,6 +68,7 @@ Rails.application.routes.draw do
     resources :deletions, only: %i[new create], module: :category
 
     post :bootstrap, on: :collection
+    delete :destroy_all, on: :collection
   end
 
   resources :budgets, only: %i[index show edit update], param: :month_year do
@@ -75,7 +77,7 @@ Rails.application.routes.draw do
     resources :budget_categories, only: %i[index show update]
   end
 
-  resources :merchants, only: %i[index new create edit update destroy]
+  resources :family_merchants, only: %i[index new create edit update destroy]
 
   resources :transfers, only: %i[new create destroy show update]
 
@@ -135,6 +137,17 @@ Rails.application.routes.draw do
     end
   end
 
+  resources :rules, except: :show do
+    member do
+      get :confirm
+      post :apply
+    end
+
+    collection do
+      delete :destroy_all
+    end
+  end
+
   # Convenience routes for polymorphic paths
   # Example: account_path(Account.new(accountable: Depository.new)) => /depositories/123
   direct :account do |model, options|
diff --git a/db/migrate/20250416235317_add_rules_engine.rb b/db/migrate/20250416235317_add_rules_engine.rb
new file mode 100644
index 00000000..960a479e
--- /dev/null
+++ b/db/migrate/20250416235317_add_rules_engine.rb
@@ -0,0 +1,33 @@
+class AddRulesEngine < ActiveRecord::Migration[7.2]
+  def change
+    create_table :rules, id: :uuid do |t|
+      t.references :family, null: false, foreign_key: true, type: :uuid
+
+      t.string :resource_type, null: false
+      t.date :effective_date
+      t.boolean :active, null: false, default: false
+      t.timestamps
+    end
+
+    create_table :rule_conditions, id: :uuid do |t|
+      t.references :rule, foreign_key: true, type: :uuid
+      t.references :parent, foreign_key: { to_table: :rule_conditions }, type: :uuid
+
+      t.string :condition_type, null: false
+      t.string :operator, null: false
+      t.string :value
+      t.timestamps
+    end
+
+    create_table :rule_actions, id: :uuid do |t|
+      t.references :rule, null: false, foreign_key: true, type: :uuid
+
+      t.string :action_type, null: false
+      t.string :value
+      t.timestamps
+    end
+
+    add_column :users, :rule_prompts_disabled, :boolean, default: false
+    add_column :users, :rule_prompt_dismissed_at, :datetime
+  end
+end
diff --git a/db/migrate/20250416235420_add_data_enrichments.rb b/db/migrate/20250416235420_add_data_enrichments.rb
new file mode 100644
index 00000000..1997461c
--- /dev/null
+++ b/db/migrate/20250416235420_add_data_enrichments.rb
@@ -0,0 +1,33 @@
+class AddDataEnrichments < ActiveRecord::Migration[7.2]
+  def change
+    create_table :data_enrichments, id: :uuid do |t|
+      t.references :enrichable, polymorphic: true, null: false, type: :uuid
+      t.string :source
+      t.string :attribute_name
+      t.jsonb :value
+      t.jsonb :metadata
+
+      t.timestamps
+    end
+
+    add_index :data_enrichments, [ :enrichable_id, :enrichable_type, :source, :attribute_name ], unique: true
+
+    # Entries
+    add_column :entries, :locked_attributes, :jsonb, default: {}
+    add_column :transactions, :locked_attributes, :jsonb, default: {}
+    add_column :trades, :locked_attributes, :jsonb, default: {}
+    add_column :valuations, :locked_attributes, :jsonb, default: {}
+
+    # Accounts
+    add_column :accounts, :locked_attributes, :jsonb, default: {}
+    add_column :depositories, :locked_attributes, :jsonb, default: {}
+    add_column :investments, :locked_attributes, :jsonb, default: {}
+    add_column :cryptos, :locked_attributes, :jsonb, default: {}
+    add_column :properties, :locked_attributes, :jsonb, default: {}
+    add_column :vehicles, :locked_attributes, :jsonb, default: {}
+    add_column :other_assets, :locked_attributes, :jsonb, default: {}
+    add_column :credit_cards, :locked_attributes, :jsonb, default: {}
+    add_column :loans, :locked_attributes, :jsonb, default: {}
+    add_column :other_liabilities, :locked_attributes, :jsonb, default: {}
+  end
+end
diff --git a/db/migrate/20250416235758_merchant_and_category_enrichment.rb b/db/migrate/20250416235758_merchant_and_category_enrichment.rb
new file mode 100644
index 00000000..2c25eeb3
--- /dev/null
+++ b/db/migrate/20250416235758_merchant_and_category_enrichment.rb
@@ -0,0 +1,34 @@
+class MerchantAndCategoryEnrichment < ActiveRecord::Migration[7.2]
+  def change
+    change_column_null :merchants, :family_id, true
+    change_column_null :merchants, :color, true
+    change_column_default :merchants, :color, from: "#e99537", to: nil
+    remove_column :merchants, :enriched_at, :datetime
+    rename_column :merchants, :icon_url, :logo_url
+
+    add_column :merchants, :website_url, :string
+    add_column :merchants, :type, :string
+    add_index :merchants, :type
+
+    reversible do |dir|
+      dir.up do
+        # All of our existing merchants are family-generated right now
+        Merchant.update_all(type: "FamilyMerchant")
+      end
+    end
+
+    change_column_null :merchants, :type, false
+
+    add_column :merchants, :source, :string
+    add_column :merchants, :provider_merchant_id, :string
+
+    add_index :merchants, [ :family_id, :name ], unique: true, where: "type = 'FamilyMerchant'"
+    add_index :merchants, [ :source, :name ], unique: true, where: "type = 'ProviderMerchant'"
+
+    add_column :transactions, :plaid_category, :string
+    add_column :transactions, :plaid_category_detailed, :string
+
+    remove_column :entries, :enriched_name, :string
+    remove_column :entries, :enriched_at, :datetime
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index 280aae75..adb03c7d 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema[7.2].define(version: 2025_04_13_141446) do
+ActiveRecord::Schema[7.2].define(version: 2025_04_16_235758) do
   # These are extensions that must be enabled in order to support this database
   enable_extension "pgcrypto"
   enable_extension "plpgsql"
@@ -36,6 +36,7 @@ ActiveRecord::Schema[7.2].define(version: 2025_04_13_141446) do
     t.boolean "scheduled_for_deletion", default: false
     t.datetime "last_synced_at"
     t.decimal "cash_balance", precision: 19, scale: 4, default: "0.0"
+    t.jsonb "locked_attributes", default: {}
     t.index ["accountable_id", "accountable_type"], name: "index_accounts_on_accountable_id_and_accountable_type"
     t.index ["accountable_type"], name: "index_accounts_on_accountable_type"
     t.index ["family_id", "accountable_type"], name: "index_accounts_on_family_id_and_accountable_type"
@@ -156,16 +157,32 @@ ActiveRecord::Schema[7.2].define(version: 2025_04_13_141446) do
     t.decimal "apr", precision: 10, scale: 2
     t.date "expiration_date"
     t.decimal "annual_fee", precision: 10, scale: 2
+    t.jsonb "locked_attributes", default: {}
   end
 
   create_table "cryptos", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
+    t.jsonb "locked_attributes", default: {}
+  end
+
+  create_table "data_enrichments", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
+    t.string "enrichable_type", null: false
+    t.uuid "enrichable_id", null: false
+    t.string "source"
+    t.string "attribute_name"
+    t.jsonb "value"
+    t.jsonb "metadata"
+    t.datetime "created_at", null: false
+    t.datetime "updated_at", null: false
+    t.index ["enrichable_id", "enrichable_type", "source", "attribute_name"], name: "idx_on_enrichable_id_enrichable_type_source_attribu_5be5f63e08", unique: true
+    t.index ["enrichable_type", "enrichable_id"], name: "index_data_enrichments_on_enrichable"
   end
 
   create_table "depositories", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
+    t.jsonb "locked_attributes", default: {}
   end
 
   create_table "entries", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
@@ -182,8 +199,7 @@ ActiveRecord::Schema[7.2].define(version: 2025_04_13_141446) do
     t.text "notes"
     t.boolean "excluded", default: false
     t.string "plaid_id"
-    t.datetime "enriched_at"
-    t.string "enriched_name"
+    t.jsonb "locked_attributes", default: {}
     t.index ["account_id"], name: "index_entries_on_account_id"
     t.index ["import_id"], name: "index_entries_on_import_id"
   end
@@ -324,6 +340,7 @@ ActiveRecord::Schema[7.2].define(version: 2025_04_13_141446) do
   create_table "investments", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
+    t.jsonb "locked_attributes", default: {}
   end
 
   create_table "invitations", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
@@ -357,17 +374,24 @@ ActiveRecord::Schema[7.2].define(version: 2025_04_13_141446) do
     t.decimal "interest_rate", precision: 10, scale: 3
     t.integer "term_months"
     t.decimal "initial_balance", precision: 19, scale: 4
+    t.jsonb "locked_attributes", default: {}
   end
 
   create_table "merchants", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
     t.string "name", null: false
-    t.string "color", default: "#e99537", null: false
-    t.uuid "family_id", null: false
+    t.string "color"
+    t.uuid "family_id"
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
-    t.string "icon_url"
-    t.datetime "enriched_at"
+    t.string "logo_url"
+    t.string "website_url"
+    t.string "type", null: false
+    t.string "source"
+    t.string "provider_merchant_id"
+    t.index ["family_id", "name"], name: "index_merchants_on_family_id_and_name", unique: true, where: "((type)::text = 'FamilyMerchant'::text)"
     t.index ["family_id"], name: "index_merchants_on_family_id"
+    t.index ["source", "name"], name: "index_merchants_on_source_and_name", unique: true, where: "((type)::text = 'ProviderMerchant'::text)"
+    t.index ["type"], name: "index_merchants_on_type"
   end
 
   create_table "messages", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
@@ -387,11 +411,13 @@ ActiveRecord::Schema[7.2].define(version: 2025_04_13_141446) do
   create_table "other_assets", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
+    t.jsonb "locked_attributes", default: {}
   end
 
   create_table "other_liabilities", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
+    t.jsonb "locked_attributes", default: {}
   end
 
   create_table "plaid_accounts", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
@@ -435,6 +461,7 @@ ActiveRecord::Schema[7.2].define(version: 2025_04_13_141446) do
     t.integer "year_built"
     t.integer "area_value"
     t.string "area_unit"
+    t.jsonb "locked_attributes", default: {}
   end
 
   create_table "rejected_transfers", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
@@ -447,6 +474,37 @@ ActiveRecord::Schema[7.2].define(version: 2025_04_13_141446) do
     t.index ["outflow_transaction_id"], name: "index_rejected_transfers_on_outflow_transaction_id"
   end
 
+  create_table "rule_actions", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
+    t.uuid "rule_id", null: false
+    t.string "action_type", null: false
+    t.string "value"
+    t.datetime "created_at", null: false
+    t.datetime "updated_at", null: false
+    t.index ["rule_id"], name: "index_rule_actions_on_rule_id"
+  end
+
+  create_table "rule_conditions", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
+    t.uuid "rule_id"
+    t.uuid "parent_id"
+    t.string "condition_type", null: false
+    t.string "operator", null: false
+    t.string "value"
+    t.datetime "created_at", null: false
+    t.datetime "updated_at", null: false
+    t.index ["parent_id"], name: "index_rule_conditions_on_parent_id"
+    t.index ["rule_id"], name: "index_rule_conditions_on_rule_id"
+  end
+
+  create_table "rules", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
+    t.uuid "family_id", null: false
+    t.string "resource_type", null: false
+    t.date "effective_date"
+    t.boolean "active", default: false, null: false
+    t.datetime "created_at", null: false
+    t.datetime "updated_at", null: false
+    t.index ["family_id"], name: "index_rules_on_family_id"
+  end
+
   create_table "securities", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
     t.string "ticker", null: false
     t.string "name"
@@ -570,6 +628,7 @@ ActiveRecord::Schema[7.2].define(version: 2025_04_13_141446) do
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
     t.string "currency"
+    t.jsonb "locked_attributes", default: {}
     t.index ["security_id"], name: "index_trades_on_security_id"
   end
 
@@ -578,6 +637,9 @@ ActiveRecord::Schema[7.2].define(version: 2025_04_13_141446) do
     t.datetime "updated_at", null: false
     t.uuid "category_id"
     t.uuid "merchant_id"
+    t.jsonb "locked_attributes", default: {}
+    t.string "plaid_category"
+    t.string "plaid_category_detailed"
     t.index ["category_id"], name: "index_transactions_on_category_id"
     t.index ["merchant_id"], name: "index_transactions_on_merchant_id"
   end
@@ -615,6 +677,8 @@ ActiveRecord::Schema[7.2].define(version: 2025_04_13_141446) do
     t.boolean "show_ai_sidebar", default: true
     t.boolean "ai_enabled", default: false, null: false
     t.string "theme", default: "system"
+    t.boolean "rule_prompts_disabled", default: false
+    t.datetime "rule_prompt_dismissed_at"
     t.index ["email"], name: "index_users_on_email", unique: true
     t.index ["family_id"], name: "index_users_on_family_id"
     t.index ["last_viewed_chat_id"], name: "index_users_on_last_viewed_chat_id"
@@ -624,6 +688,7 @@ ActiveRecord::Schema[7.2].define(version: 2025_04_13_141446) do
   create_table "valuations", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
+    t.jsonb "locked_attributes", default: {}
   end
 
   create_table "vehicles", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
@@ -634,6 +699,7 @@ ActiveRecord::Schema[7.2].define(version: 2025_04_13_141446) do
     t.string "mileage_unit"
     t.string "make"
     t.string "model"
+    t.jsonb "locked_attributes", default: {}
   end
 
   add_foreign_key "accounts", "families"
@@ -664,6 +730,10 @@ ActiveRecord::Schema[7.2].define(version: 2025_04_13_141446) do
   add_foreign_key "plaid_items", "families"
   add_foreign_key "rejected_transfers", "transactions", column: "inflow_transaction_id"
   add_foreign_key "rejected_transfers", "transactions", column: "outflow_transaction_id"
+  add_foreign_key "rule_actions", "rules"
+  add_foreign_key "rule_conditions", "rule_conditions", column: "parent_id"
+  add_foreign_key "rule_conditions", "rules"
+  add_foreign_key "rules", "families"
   add_foreign_key "security_prices", "securities"
   add_foreign_key "sessions", "impersonation_sessions", column: "active_impersonator_session_id"
   add_foreign_key "sessions", "users"
diff --git a/test/controllers/categories_controller_test.rb b/test/controllers/categories_controller_test.rb
index 5ec08b41..2cbb46f5 100644
--- a/test/controllers/categories_controller_test.rb
+++ b/test/controllers/categories_controller_test.rb
@@ -84,7 +84,7 @@ class CategoriesControllerTest < ActionDispatch::IntegrationTest
   end
 
   test "bootstrap" do
-    assert_difference "Category.count", 10 do
+    assert_difference "Category.count", 12 do
       post bootstrap_categories_url
     end
 
diff --git a/test/controllers/family_merchants_controller_test.rb b/test/controllers/family_merchants_controller_test.rb
new file mode 100644
index 00000000..eda482a1
--- /dev/null
+++ b/test/controllers/family_merchants_controller_test.rb
@@ -0,0 +1,39 @@
+require "test_helper"
+
+class FamilyMerchantsControllerTest < ActionDispatch::IntegrationTest
+  setup do
+    sign_in @user = users(:family_admin)
+    @merchant = merchants(:netflix)
+  end
+
+  test "index" do
+    get family_merchants_path
+    assert_response :success
+  end
+
+  test "new" do
+    get new_family_merchant_path
+    assert_response :success
+  end
+
+  test "should create merchant" do
+    assert_difference("FamilyMerchant.count") do
+      post family_merchants_url, params: { family_merchant: { name: "new merchant", color: "#000000" } }
+    end
+
+    assert_redirected_to family_merchants_path
+  end
+
+  test "should update merchant" do
+    patch family_merchant_url(@merchant), params: { family_merchant: { name: "new name", color: "#000000" } }
+    assert_redirected_to family_merchants_path
+  end
+
+  test "should destroy merchant" do
+    assert_difference("FamilyMerchant.count", -1) do
+      delete family_merchant_url(@merchant)
+    end
+
+    assert_redirected_to family_merchants_path
+  end
+end
diff --git a/test/controllers/merchants_controller_test.rb b/test/controllers/merchants_controller_test.rb
deleted file mode 100644
index 4f84bb0d..00000000
--- a/test/controllers/merchants_controller_test.rb
+++ /dev/null
@@ -1,39 +0,0 @@
-require "test_helper"
-
-class MerchantsControllerTest < ActionDispatch::IntegrationTest
-  setup do
-    sign_in @user = users(:family_admin)
-    @merchant = merchants(:netflix)
-  end
-
-  test "index" do
-    get merchants_path
-    assert_response :success
-  end
-
-  test "new" do
-    get new_merchant_path
-    assert_response :success
-  end
-
-  test "should create merchant" do
-    assert_difference("Merchant.count") do
-      post merchants_url, params: { merchant: { name: "new merchant", color: "#000000" } }
-    end
-
-    assert_redirected_to merchants_path
-  end
-
-  test "should update merchant" do
-    patch merchant_url(@merchant), params: { merchant: { name: "new name", color: "#000000" } }
-    assert_redirected_to merchants_path
-  end
-
-  test "should destroy merchant" do
-    assert_difference("Merchant.count", -1) do
-      delete merchant_url(@merchant)
-    end
-
-    assert_redirected_to merchants_path
-  end
-end
diff --git a/test/controllers/rules_controller_test.rb b/test/controllers/rules_controller_test.rb
new file mode 100644
index 00000000..cb5f8a0d
--- /dev/null
+++ b/test/controllers/rules_controller_test.rb
@@ -0,0 +1,165 @@
+require "test_helper"
+
+class RulesControllerTest < ActionDispatch::IntegrationTest
+  setup do
+    sign_in @user = users(:family_admin)
+  end
+
+  test "should get new" do
+    get new_rule_url(resource_type: "transaction")
+    assert_response :success
+  end
+
+  test "should get edit" do
+    get edit_rule_url(rules(:one))
+    assert_response :success
+  end
+
+  # "Set all transactions with a name like 'starbucks' and an amount between 20 and 40 to the 'food and drink' category"
+  test "creates rule with nested conditions" do
+    post rules_url, params: {
+      rule: {
+        effective_date: 30.days.ago.to_date,
+        resource_type: "transaction",
+        conditions_attributes: {
+          "0" => {
+            condition_type: "transaction_name",
+            operator: "like",
+            value: "starbucks"
+          },
+          "1" => {
+            condition_type: "compound",
+            operator: "and",
+            sub_conditions_attributes: {
+              "0" => {
+                condition_type: "transaction_amount",
+                operator: ">",
+                value: 20
+              },
+              "1" => {
+                condition_type: "transaction_amount",
+                operator: "<",
+                value: 40
+              }
+            }
+          }
+        },
+        actions_attributes: {
+          "0" => {
+            action_type: "set_transaction_category",
+            value: categories(:food_and_drink).id
+          }
+        }
+      }
+    }
+
+    rule = @user.family.rules.order("created_at DESC").first
+
+    # Rule
+    assert_equal "transaction", rule.resource_type
+    assert_not rule.active # Not active by default
+    assert_equal 30.days.ago.to_date, rule.effective_date
+
+    # Conditions assertions
+    assert_equal 2, rule.conditions.count
+    compound_condition = rule.conditions.find { |condition| condition.condition_type == "compound" }
+    assert_equal "compound", compound_condition.condition_type
+    assert_equal 2, compound_condition.sub_conditions.count
+
+    # Actions assertions
+    assert_equal 1, rule.actions.count
+    assert_equal "set_transaction_category", rule.actions.first.action_type
+    assert_equal categories(:food_and_drink).id, rule.actions.first.value
+
+    assert_redirected_to confirm_rule_url(rule)
+  end
+
+  test "can update rule" do
+    rule = rules(:one)
+
+    assert_difference -> { Rule.count } => 0,
+      -> { Rule::Condition.count } => 1,
+      -> { Rule::Action.count } => 1 do
+      patch rule_url(rule), params: {
+        rule: {
+          active: false,
+          conditions_attributes: {
+            "0" => {
+              id: rule.conditions.first.id,
+              value: "new_value"
+            },
+            "1" => {
+              condition_type: "transaction_amount",
+              operator: ">",
+              value: 100
+            }
+          },
+          actions_attributes: {
+            "0" => {
+              id: rule.actions.first.id,
+              value: "new_value"
+            },
+            "1" => {
+              action_type: "set_transaction_tags",
+              value: tags(:one).id
+            }
+          }
+        }
+      }
+    end
+
+    rule.reload
+
+    assert_not rule.active
+    assert_equal "new_value", rule.conditions.order("created_at ASC").first.value
+    assert_equal "new_value", rule.actions.order("created_at ASC").first.value
+    assert_equal tags(:one).id, rule.actions.order("created_at ASC").last.value
+    assert_equal "100", rule.conditions.order("created_at ASC").last.value
+
+    assert_redirected_to rules_url
+  end
+
+  test "can destroy conditions and actions while editing" do
+    rule = rules(:one)
+
+    assert_equal 1, rule.conditions.count
+    assert_equal 1, rule.actions.count
+
+    patch rule_url(rule), params: {
+      rule: {
+        conditions_attributes: {
+          "0" => { id: rule.conditions.first.id, _destroy: true },
+          "1" => {
+            condition_type: "transaction_name",
+            operator: "like",
+            value: "new_condition"
+          }
+        },
+        actions_attributes: {
+          "0" => { id: rule.actions.first.id, _destroy: true },
+          "1" => {
+            action_type: "set_transaction_tags",
+            value: tags(:one).id
+          }
+        }
+      }
+    }
+
+    assert_redirected_to rules_url
+
+    rule.reload
+
+    assert_equal 1, rule.conditions.count
+    assert_equal 1, rule.actions.count
+  end
+
+  test "can destroy rule" do
+    rule = rules(:one)
+
+    assert_difference [ "Rule.count", "Rule::Condition.count", "Rule::Action.count" ], -1 do
+      delete rule_url(rule)
+    end
+
+    assert_redirected_to rules_url
+  end
+end
diff --git a/test/fixtures/merchants.yml b/test/fixtures/merchants.yml
index 3e3ca05a..6ac64ef4 100644
--- a/test/fixtures/merchants.yml
+++ b/test/fixtures/merchants.yml
@@ -1,13 +1,16 @@
 one:
+  type: FamilyMerchant
   name: Test
   family: empty
 
 netflix:
+  type: FamilyMerchant
   name: Netflix
   color: "#fd7f6f"
   family: dylan_family
 
 amazon:
+  type: FamilyMerchant
   name: Amazon
   color: "#fd7f6f"
   family: dylan_family
diff --git a/test/fixtures/rule/actions.yml b/test/fixtures/rule/actions.yml
new file mode 100644
index 00000000..4a56bf29
--- /dev/null
+++ b/test/fixtures/rule/actions.yml
@@ -0,0 +1,4 @@
+one:
+  rule: one
+  action_type: set_transaction_category
+  value: "some_category_id"
\ No newline at end of file
diff --git a/test/fixtures/rule/conditions.yml b/test/fixtures/rule/conditions.yml
new file mode 100644
index 00000000..3c140f45
--- /dev/null
+++ b/test/fixtures/rule/conditions.yml
@@ -0,0 +1,5 @@
+one:
+  rule: one
+  condition_type: transaction_name
+  operator: like
+  value: "starbucks"
diff --git a/test/fixtures/rules.yml b/test/fixtures/rules.yml
new file mode 100644
index 00000000..db7a3566
--- /dev/null
+++ b/test/fixtures/rules.yml
@@ -0,0 +1,3 @@
+one:
+  family: dylan_family
+  resource_type: "transaction"
\ No newline at end of file
diff --git a/test/models/family/auto_categorizer_test.rb b/test/models/family/auto_categorizer_test.rb
new file mode 100644
index 00000000..c9440919
--- /dev/null
+++ b/test/models/family/auto_categorizer_test.rb
@@ -0,0 +1,42 @@
+require "test_helper"
+
+class Family::AutoCategorizerTest < ActiveSupport::TestCase
+  include EntriesTestHelper, ProviderTestHelper
+
+  setup do
+    @family = families(:dylan_family)
+    @account = @family.accounts.create!(name: "Rule test", balance: 100, currency: "USD", accountable: Depository.new)
+    @llm_provider = mock
+    Provider::Registry.stubs(:get_provider).with(:openai).returns(@llm_provider)
+  end
+
+  test "auto-categorizes transactions" do
+    txn1 = create_transaction(account: @account, name: "McDonalds").transaction
+    txn2 = create_transaction(account: @account, name: "Amazon purchase").transaction
+    txn3 = create_transaction(account: @account, name: "Netflix subscription").transaction
+
+    test_category = @family.categories.create!(name: "Test category")
+
+    provider_response = provider_success_response([
+      AutoCategorization.new(transaction_id: txn1.id, category_name: test_category.name),
+      AutoCategorization.new(transaction_id: txn2.id, category_name: test_category.name),
+      AutoCategorization.new(transaction_id: txn3.id, category_name: nil)
+    ])
+
+    @llm_provider.expects(:auto_categorize).returns(provider_response).once
+
+    assert_difference "DataEnrichment.count", 2 do
+      Family::AutoCategorizer.new(@family, transaction_ids: [ txn1.id, txn2.id, txn3.id ]).auto_categorize
+    end
+
+    assert_equal test_category, txn1.reload.category
+    assert_equal test_category, txn2.reload.category
+    assert_nil txn3.reload.category
+
+    # After auto-categorization, all transactions are locked and no longer enrichable
+    assert_equal 0, @account.transactions.reload.enrichable(:category_id).count
+  end
+
+  private
+    AutoCategorization = Provider::LlmConcept::AutoCategorization
+end
diff --git a/test/models/family/auto_merchant_detector_test.rb b/test/models/family/auto_merchant_detector_test.rb
new file mode 100644
index 00000000..69c8e3cd
--- /dev/null
+++ b/test/models/family/auto_merchant_detector_test.rb
@@ -0,0 +1,42 @@
+require "test_helper"
+
+class Family::AutoMerchantDetectorTest < ActiveSupport::TestCase
+  include EntriesTestHelper, ProviderTestHelper
+
+  setup do
+    @family = families(:dylan_family)
+    @account = @family.accounts.create!(name: "Rule test", balance: 100, currency: "USD", accountable: Depository.new)
+    @llm_provider = mock
+    Provider::Registry.stubs(:get_provider).with(:openai).returns(@llm_provider)
+  end
+
+  test "auto detects transaction merchants" do
+    txn1 = create_transaction(account: @account, name: "McDonalds").transaction
+    txn2 = create_transaction(account: @account, name: "Chipotle").transaction
+    txn3 = create_transaction(account: @account, name: "generic").transaction
+
+    provider_response = provider_success_response([
+      AutoDetectedMerchant.new(transaction_id: txn1.id, business_name: "McDonalds", business_url: "mcdonalds.com"),
+      AutoDetectedMerchant.new(transaction_id: txn2.id, business_name: "Chipotle", business_url: "chipotle.com"),
+      AutoDetectedMerchant.new(transaction_id: txn3.id, business_name: nil, business_url: nil)
+    ])
+
+    @llm_provider.expects(:auto_detect_merchants).returns(provider_response).once
+
+    assert_difference "DataEnrichment.count", 2 do
+      Family::AutoMerchantDetector.new(@family, transaction_ids: [ txn1.id, txn2.id, txn3.id ]).auto_detect
+    end
+
+    assert_equal "McDonalds", txn1.reload.merchant.name
+    assert_equal "Chipotle", txn2.reload.merchant.name
+    assert_equal "https://logo.synthfinance.com/mcdonalds.com", txn1.reload.merchant.logo_url
+    assert_equal "https://logo.synthfinance.com/chipotle.com", txn2.reload.merchant.logo_url
+    assert_nil txn3.reload.merchant
+
+    # After auto-detection, all transactions are locked and no longer enrichable
+    assert_equal 0, @account.transactions.reload.enrichable(:merchant_id).count
+  end
+
+  private
+    AutoDetectedMerchant = Provider::LlmConcept::AutoDetectedMerchant
+end
diff --git a/test/models/provider/openai_test.rb b/test/models/provider/openai_test.rb
index e6384297..f9cf3117 100644
--- a/test/models/provider/openai_test.rb
+++ b/test/models/provider/openai_test.rb
@@ -17,6 +17,103 @@ class Provider::OpenaiTest < ActiveSupport::TestCase
     end
   end
 
+  test "auto categorizes transactions by various attributes" do
+    VCR.use_cassette("openai/auto_categorize") do
+      input_transactions = [
+        { id: "1", name: "McDonalds", amount: 20, classification: "expense", merchant: "McDonalds", hint: "Fast Food" },
+        { id: "2", name: "Amazon purchase", amount: 100, classification: "expense", merchant: "Amazon" },
+        { id: "3", name: "Netflix subscription", amount: 10, classification: "expense", merchant: "Netflix", hint: "Subscriptions" },
+        { id: "4", name: "paycheck", amount: 3000, classification: "income" },
+        { id: "5", name: "Italian dinner with friends", amount: 100, classification: "expense" },
+        { id: "6", name: "1212XXXBCaaa charge", amount: 2.99, classification: "expense" }
+      ]
+
+      response = @subject.auto_categorize(
+        transactions: input_transactions,
+        user_categories: [
+          { id: "shopping_id", name: "Shopping", is_subcategory: false, parent_id: nil, classification: "expense" },
+          { id: "subscriptions_id", name: "Subscriptions", is_subcategory: true, parent_id: nil, classification: "expense" },
+          { id: "restaurants_id", name: "Restaurants", is_subcategory: false, parent_id: nil, classification: "expense" },
+          { id: "fast_food_id", name: "Fast Food", is_subcategory: true, parent_id: "restaurants_id", classification: "expense" },
+          { id: "income_id", name: "Income", is_subcategory: false, parent_id: nil, classification: "income" }
+        ]
+      )
+
+      assert response.success?
+      assert_equal input_transactions.size, response.data.size
+
+      txn1 = response.data.find { |c| c.transaction_id == "1" }
+      txn2 = response.data.find { |c| c.transaction_id == "2" }
+      txn3 = response.data.find { |c| c.transaction_id == "3" }
+      txn4 = response.data.find { |c| c.transaction_id == "4" }
+      txn5 = response.data.find { |c| c.transaction_id == "5" }
+      txn6 = response.data.find { |c| c.transaction_id == "6" }
+
+      assert_equal "Fast Food", txn1.category_name
+      assert_equal "Shopping", txn2.category_name
+      assert_equal "Subscriptions", txn3.category_name
+      assert_equal "Income", txn4.category_name
+      assert_equal "Restaurants", txn5.category_name
+      assert_nil txn6.category_name
+    end
+  end
+
+  test "auto detects merchants" do
+    VCR.use_cassette("openai/auto_detect_merchants") do
+      input_transactions = [
+        { id: "1", name: "McDonalds", amount: 20, classification: "expense" },
+        { id: "2", name: "local pub", amount: 20, classification: "expense" },
+        { id: "3", name: "WMT purchases", amount: 20, classification: "expense" },
+        { id: "4", name: "amzn 123 abc", amount: 20, classification: "expense" },
+        { id: "5", name: "chaseX1231", amount: 2000, classification: "income" },
+        { id: "6", name: "check deposit 022", amount: 200, classification: "income" },
+        { id: "7", name: "shooters bar and grill", amount: 200, classification: "expense" },
+        { id: "8", name: "Microsoft Office subscription", amount: 200, classification: "expense" }
+      ]
+
+      response = @subject.auto_detect_merchants(
+        transactions: input_transactions,
+        user_merchants: [ { name: "Shooters" } ]
+      )
+
+      assert response.success?
+      assert_equal input_transactions.size, response.data.size
+
+      txn1 = response.data.find { |c| c.transaction_id == "1" }
+      txn2 = response.data.find { |c| c.transaction_id == "2" }
+      txn3 = response.data.find { |c| c.transaction_id == "3" }
+      txn4 = response.data.find { |c| c.transaction_id == "4" }
+      txn5 = response.data.find { |c| c.transaction_id == "5" }
+      txn6 = response.data.find { |c| c.transaction_id == "6" }
+      txn7 = response.data.find { |c| c.transaction_id == "7" }
+      txn8 = response.data.find { |c| c.transaction_id == "8" }
+
+      assert_equal "McDonald's", txn1.business_name
+      assert_equal "mcdonalds.com", txn1.business_url
+
+      assert_nil txn2.business_name
+      assert_nil txn2.business_url
+
+      assert_equal "Walmart", txn3.business_name
+      assert_equal "walmart.com", txn3.business_url
+
+      assert_equal "Amazon", txn4.business_name
+      assert_equal "amazon.com", txn4.business_url
+
+      assert_nil txn5.business_name
+      assert_nil txn5.business_url
+
+      assert_nil txn6.business_name
+      assert_nil txn6.business_url
+
+      assert_equal "Shooters", txn7.business_name
+      assert_nil txn7.business_url
+
+      assert_equal "Microsoft", txn8.business_name
+      assert_equal "microsoft.com", txn8.business_url
+    end
+  end
+
   test "basic chat response" do
     VCR.use_cassette("openai/chat/basic_response") do
       response = @subject.chat_response(
diff --git a/test/models/provider/plaid/category_alias_matcher_test.rb b/test/models/provider/plaid/category_alias_matcher_test.rb
new file mode 100644
index 00000000..11881dea
--- /dev/null
+++ b/test/models/provider/plaid/category_alias_matcher_test.rb
@@ -0,0 +1,136 @@
+require "test_helper"
+
+class Provider::Plaid::CategoryAliasMatcherTest < ActiveSupport::TestCase
+  setup do
+    @family = families(:empty)
+
+    # User income categories
+    @income = @family.categories.create!(name: "Income", classification: "income")
+    @dividend_income = @family.categories.create!(name: "Dividend Income", parent: @income, classification: "income")
+    @interest_income = @family.categories.create!(name: "Interest Income", parent: @income, classification: "income")
+
+    # User expense categories
+    @loan_payments = @family.categories.create!(name: "Loan Payments")
+    @fees = @family.categories.create!(name: "Fees")
+    @entertainment = @family.categories.create!(name: "Entertainment")
+
+    @food_and_drink = @family.categories.create!(name: "Food & Drink")
+    @groceries = @family.categories.create!(name: "Groceries", parent: @food_and_drink)
+    @restaurant = @family.categories.create!(name: "Restaurant", parent: @food_and_drink)
+
+    @shopping = @family.categories.create!(name: "Shopping")
+    @clothing = @family.categories.create!(name: "Clothing", parent: @shopping)
+
+    @home = @family.categories.create!(name: "Home")
+    @medical = @family.categories.create!(name: "Medical")
+    @personal_care = @family.categories.create!(name: "Personal Care")
+    @transportation = @family.categories.create!(name: "Transportation")
+    @trips = @family.categories.create!(name: "Trips")
+
+    @services = @family.categories.create!(name: "Services")
+    @car = @family.categories.create!(name: "Car", parent: @services)
+
+    @giving = @family.categories.create!(name: "Giving")
+
+    @matcher = Provider::Plaid::CategoryAliasMatcher.new(@family.categories)
+  end
+
+  test "matches expense categories" do
+    assert_equal @loan_payments, @matcher.match("loan_payments_car_payment")
+    assert_equal @loan_payments, @matcher.match("loan_payments_credit_card_payment")
+    assert_equal @loan_payments, @matcher.match("loan_payments_personal_loan_payment")
+    assert_equal @loan_payments, @matcher.match("loan_payments_mortgage_payment")
+    assert_equal @loan_payments, @matcher.match("loan_payments_student_loan_payment")
+    assert_equal @loan_payments, @matcher.match("loan_payments_other_payment")
+    assert_equal @fees, @matcher.match("bank_fees_atm_fees")
+    assert_equal @fees, @matcher.match("bank_fees_foreign_transaction_fees")
+    assert_equal @fees, @matcher.match("bank_fees_insufficient_funds")
+    assert_equal @fees, @matcher.match("bank_fees_interest_charge")
+    assert_equal @fees, @matcher.match("bank_fees_overdraft_fees")
+    assert_equal @fees, @matcher.match("bank_fees_other_bank_fees")
+    assert_equal @entertainment, @matcher.match("entertainment_casinos_and_gambling")
+    assert_equal @entertainment, @matcher.match("entertainment_music_and_audio")
+    assert_equal @entertainment, @matcher.match("entertainment_sporting_events_amusement_parks_and_museums")
+    assert_equal @entertainment, @matcher.match("entertainment_tv_and_movies")
+    assert_equal @entertainment, @matcher.match("entertainment_video_games")
+    assert_equal @entertainment, @matcher.match("entertainment_other_entertainment")
+    assert_equal @food_and_drink, @matcher.match("food_and_drink_beer_wine_and_liquor")
+    assert_equal @food_and_drink, @matcher.match("food_and_drink_coffee")
+    assert_equal @food_and_drink, @matcher.match("food_and_drink_fast_food")
+    assert_equal @groceries, @matcher.match("food_and_drink_groceries")
+    assert_equal @restaurant, @matcher.match("food_and_drink_restaurant")
+    assert_equal @food_and_drink, @matcher.match("food_and_drink_vending_machines")
+    assert_equal @food_and_drink, @matcher.match("food_and_drink_other_food_and_drink")
+    assert_equal @shopping, @matcher.match("general_merchandise_bookstores_and_newsstands")
+    assert_equal @clothing, @matcher.match("general_merchandise_clothing_and_accessories")
+    assert_equal @shopping, @matcher.match("general_merchandise_convenience_stores")
+    assert_equal @shopping, @matcher.match("general_merchandise_department_stores")
+    assert_equal @shopping, @matcher.match("general_merchandise_discount_stores")
+    assert_equal @shopping, @matcher.match("general_merchandise_electronics")
+    assert_equal @shopping, @matcher.match("general_merchandise_gifts_and_novelties")
+    assert_equal @shopping, @matcher.match("general_merchandise_office_supplies")
+    assert_equal @shopping, @matcher.match("general_merchandise_online_marketplaces")
+    assert_equal @shopping, @matcher.match("general_merchandise_pet_supplies")
+    assert_equal @shopping, @matcher.match("general_merchandise_sporting_goods")
+    assert_equal @shopping, @matcher.match("general_merchandise_superstores")
+    assert_equal @shopping, @matcher.match("general_merchandise_tobacco_and_vape")
+    assert_equal @shopping, @matcher.match("general_merchandise_other_general_merchandise")
+    assert_equal @home, @matcher.match("home_improvement_furniture")
+    assert_equal @home, @matcher.match("home_improvement_hardware")
+    assert_equal @home, @matcher.match("home_improvement_repair_and_maintenance")
+    assert_equal @home, @matcher.match("home_improvement_security")
+    assert_equal @home, @matcher.match("home_improvement_other_home_improvement")
+    assert_equal @medical, @matcher.match("medical_dental_care")
+    assert_equal @medical, @matcher.match("medical_eye_care")
+    assert_equal @medical, @matcher.match("medical_nursing_care")
+    assert_equal @medical, @matcher.match("medical_pharmacies_and_supplements")
+    assert_equal @medical, @matcher.match("medical_primary_care")
+    assert_equal @medical, @matcher.match("medical_veterinary_services")
+    assert_equal @medical, @matcher.match("medical_other_medical")
+    assert_equal @personal_care, @matcher.match("personal_care_gyms_and_fitness_centers")
+    assert_equal @personal_care, @matcher.match("personal_care_hair_and_beauty")
+    assert_equal @personal_care, @matcher.match("personal_care_laundry_and_dry_cleaning")
+    assert_equal @personal_care, @matcher.match("personal_care_other_personal_care")
+    assert_equal @services, @matcher.match("general_services_accounting_and_financial_planning")
+    assert_equal @car, @matcher.match("general_services_automotive")
+    assert_equal @services, @matcher.match("general_services_childcare")
+    assert_equal @services, @matcher.match("general_services_consulting_and_legal")
+    assert_equal @services, @matcher.match("general_services_education")
+    assert_equal @services, @matcher.match("general_services_insurance")
+    assert_equal @services, @matcher.match("general_services_postage_and_shipping")
+    assert_equal @services, @matcher.match("general_services_storage")
+    assert_equal @services, @matcher.match("general_services_other_general_services")
+    assert_equal @giving, @matcher.match("government_and_non_profit_donations")
+    assert_nil @matcher.match("government_and_non_profit_government_departments_and_agencies")
+    assert_nil @matcher.match("government_and_non_profit_tax_payment")
+    assert_nil @matcher.match("government_and_non_profit_other_government_and_non_profit")
+    assert_equal @transportation, @matcher.match("transportation_bikes_and_scooters")
+    assert_equal @transportation, @matcher.match("transportation_gas")
+    assert_equal @transportation, @matcher.match("transportation_parking")
+    assert_equal @transportation, @matcher.match("transportation_public_transit")
+    assert_equal @transportation, @matcher.match("transportation_taxis_and_ride_shares")
+    assert_equal @transportation, @matcher.match("transportation_tolls")
+    assert_equal @transportation, @matcher.match("transportation_other_transportation")
+    assert_equal @trips, @matcher.match("travel_flights")
+    assert_equal @trips, @matcher.match("travel_lodging")
+    assert_equal @trips, @matcher.match("travel_rental_cars")
+    assert_equal @trips, @matcher.match("travel_other_travel")
+    assert_equal @home, @matcher.match("rent_and_utilities_gas_and_electricity")
+    assert_equal @home, @matcher.match("rent_and_utilities_internet_and_cable")
+    assert_equal @home, @matcher.match("rent_and_utilities_rent")
+    assert_equal @home, @matcher.match("rent_and_utilities_sewage_and_waste_management")
+    assert_equal @home, @matcher.match("rent_and_utilities_telephone")
+    assert_equal @home, @matcher.match("rent_and_utilities_water")
+    assert_equal @home, @matcher.match("rent_and_utilities_other_utilities")
+  end
+
+  test "matches income categories" do
+    assert_equal @dividend_income, @matcher.match("income_dividends")
+    assert_equal @interest_income, @matcher.match("income_interest_earned")
+    assert_equal @income, @matcher.match("income_tax_refund")
+    assert_equal @income, @matcher.match("income_retirement_pension")
+    assert_equal @income, @matcher.match("income_unemployment")
+    assert_equal @income, @matcher.match("income_wages")
+    assert_equal @income, @matcher.match("income_other_income")
+  end
+end
diff --git a/test/models/provider/synth_test.rb b/test/models/provider/synth_test.rb
index b489d136..5dfa3bed 100644
--- a/test/models/provider/synth_test.rb
+++ b/test/models/provider/synth_test.rb
@@ -23,21 +23,4 @@ class Provider::SynthTest < ActiveSupport::TestCase
       assert usage.plan.present?
     end
   end
-
-  test "enriches transaction" do
-    VCR.use_cassette("synth/transaction_enrich") do
-      response = @synth.enrich_transaction(
-        "UBER EATS",
-        amount: 25.50,
-        date: Date.iso8601("2025-03-16"),
-        city: "San Francisco",
-        state: "CA",
-        country: "US"
-      )
-
-      data = response.data
-      assert data.name.present?
-      assert data.category.present?
-    end
-  end
 end
diff --git a/test/models/rule/action_test.rb b/test/models/rule/action_test.rb
new file mode 100644
index 00000000..6cab0bd9
--- /dev/null
+++ b/test/models/rule/action_test.rb
@@ -0,0 +1,61 @@
+require "test_helper"
+
+class Rule::ActionTest < ActiveSupport::TestCase
+  include EntriesTestHelper
+
+  setup do
+    @family = families(:dylan_family)
+    @transaction_rule = rules(:one)
+    @account = @family.accounts.create!(name: "Rule test", balance: 1000, currency: "USD", accountable: Depository.new)
+
+    @grocery_category = @family.categories.create!(name: "Grocery")
+    @whole_foods_merchant = @family.merchants.create!(name: "Whole Foods", type: "FamilyMerchant")
+
+    # Some sample transactions to work with
+    @txn1 = create_transaction(date: Date.current, account: @account, amount: 100, name: "Rule test transaction1", merchant: @whole_foods_merchant).transaction
+    @txn2 = create_transaction(date: Date.current, account: @account, amount: -200, name: "Rule test transaction2").transaction
+    @txn3 = create_transaction(date: 1.day.ago.to_date, account: @account, amount: 50, name: "Rule test transaction3").transaction
+
+    @rule_scope = @account.transactions
+  end
+
+  test "set_transaction_category" do
+    # Does not modify transactions that are locked (user edited them)
+    @txn1.lock!(:category_id)
+
+    action = Rule::Action.new(
+      rule: @transaction_rule,
+      action_type: "set_transaction_category",
+      value: @grocery_category.id
+    )
+
+    action.apply(@rule_scope)
+
+    assert_nil @txn1.reload.category
+
+    [ @txn2, @txn3 ].each do |transaction|
+      assert_equal @grocery_category.id, transaction.reload.category_id
+    end
+  end
+
+  test "set_transaction_tags" do
+    tag = @family.tags.create!(name: "Rule test tag")
+
+    # Does not modify transactions that are locked (user edited them)
+    @txn1.lock!(:tag_ids)
+
+    action = Rule::Action.new(
+      rule: @transaction_rule,
+      action_type: "set_transaction_tags",
+      value: tag.id
+    )
+
+    action.apply(@rule_scope)
+
+    assert_equal [], @txn1.reload.tags
+
+    [ @txn2, @txn3 ].each do |transaction|
+      assert_equal [ tag ], transaction.reload.tags
+    end
+  end
+end
diff --git a/test/models/rule/condition_test.rb b/test/models/rule/condition_test.rb
new file mode 100644
index 00000000..3010673d
--- /dev/null
+++ b/test/models/rule/condition_test.rb
@@ -0,0 +1,128 @@
+require "test_helper"
+
+class Rule::ConditionTest < ActiveSupport::TestCase
+  include EntriesTestHelper
+
+  setup do
+    @family = families(:empty)
+    @transaction_rule = rules(:one)
+    @account = @family.accounts.create!(name: "Rule test", balance: 1000, currency: "USD", accountable: Depository.new)
+
+    @grocery_category = @family.categories.create!(name: "Grocery")
+    @whole_foods_merchant = @family.merchants.create!(name: "Whole Foods", type: "FamilyMerchant")
+
+    # Some sample transactions to work with
+    create_transaction(date: Date.current, account: @account, amount: 100, name: "Rule test transaction1", merchant: @whole_foods_merchant)
+    create_transaction(date: Date.current, account: @account, amount: -200, name: "Rule test transaction2")
+    create_transaction(date: 1.day.ago.to_date, account: @account, amount: 50, name: "Rule test transaction3")
+    create_transaction(date: 1.year.ago.to_date, account: @account, amount: 10, name: "Rule test transaction4", merchant: @whole_foods_merchant)
+    create_transaction(date: 1.year.ago.to_date, account: @account, amount: 1000, name: "Rule test transaction5")
+
+    @rule_scope = @account.transactions
+  end
+
+  test "applies transaction_name condition" do
+    scope = @rule_scope
+
+    condition = Rule::Condition.new(
+      rule: @transaction_rule,
+      condition_type: "transaction_name",
+      operator: "=",
+      value: "Rule test transaction1"
+    )
+
+    scope = condition.prepare(scope)
+
+    assert_equal 5, scope.count
+
+    filtered = condition.apply(scope)
+
+    assert_equal 1, filtered.count
+  end
+
+  test "applies transaction_amount condition using absolute values" do
+    scope = @rule_scope
+
+    condition = Rule::Condition.new(
+      rule: @transaction_rule,
+      condition_type: "transaction_amount",
+      operator: ">",
+      value: "50"
+    )
+
+    scope = condition.prepare(scope)
+
+    filtered = condition.apply(scope)
+    assert_equal 3, filtered.count
+  end
+
+  test "applies transaction_merchant condition" do
+    scope = @rule_scope
+
+    condition = Rule::Condition.new(
+      rule: @transaction_rule,
+      condition_type: "transaction_merchant",
+      operator: "=",
+      value: @whole_foods_merchant.id
+    )
+
+    scope = condition.prepare(scope)
+
+    filtered = condition.apply(scope)
+    assert_equal 2, filtered.count
+  end
+
+  test "applies compound and condition" do
+    scope = @rule_scope
+
+    parent_condition = Rule::Condition.new(
+      rule: @transaction_rule,
+      condition_type: "compound",
+      operator: "and",
+      sub_conditions: [
+        Rule::Condition.new(
+          condition_type: "transaction_merchant",
+          operator: "=",
+          value: @whole_foods_merchant.id
+        ),
+        Rule::Condition.new(
+          condition_type: "transaction_amount",
+          operator: "<",
+          value: "50"
+        )
+      ]
+    )
+
+    scope = parent_condition.prepare(scope)
+
+    filtered = parent_condition.apply(scope)
+    assert_equal 1, filtered.count
+  end
+
+  test "applies compound or condition" do
+    scope = @rule_scope
+
+    parent_condition = Rule::Condition.new(
+      rule: @transaction_rule,
+      condition_type: "compound",
+      operator: "or",
+      sub_conditions: [
+        Rule::Condition.new(
+          condition_type: "transaction_merchant",
+          operator: "=",
+          value: @whole_foods_merchant.id
+        ),
+        Rule::Condition.new(
+          condition_type: "transaction_amount",
+          operator: "<",
+          value: "50"
+        )
+      ]
+    )
+
+    scope = parent_condition.prepare(scope)
+
+    filtered = parent_condition.apply(scope)
+    assert_equal 2, filtered.count
+  end
+end
diff --git a/test/models/rule_test.rb b/test/models/rule_test.rb
new file mode 100644
index 00000000..5cddc644
--- /dev/null
+++ b/test/models/rule_test.rb
@@ -0,0 +1,77 @@
+require "test_helper"
+
+class RuleTest < ActiveSupport::TestCase
+  include EntriesTestHelper
+
+  setup do
+    @family = families(:empty)
+    @account = @family.accounts.create!(name: "Rule test", balance: 1000, currency: "USD", accountable: Depository.new)
+    @whole_foods_merchant = @family.merchants.create!(name: "Whole Foods", type: "FamilyMerchant")
+    @groceries_category = @family.categories.create!(name: "Groceries")
+  end
+
+  test "basic rule" do
+    transaction_entry = create_transaction(date: Date.current, account: @account, merchant: @whole_foods_merchant)
+
+    rule = Rule.create!(
+      family: @family,
+      resource_type: "transaction",
+      effective_date: 1.day.ago.to_date,
+      conditions: [ Rule::Condition.new(condition_type: "transaction_merchant", operator: "=", value: @whole_foods_merchant.id) ],
+      actions: [ Rule::Action.new(action_type: "set_transaction_category", value: @groceries_category.id) ]
+    )
+
+    rule.apply
+
+    transaction_entry.reload
+
+    assert_equal @groceries_category, transaction_entry.transaction.category
+  end
+
+  test "compound rule" do
+    transaction_entry1 = create_transaction(date: Date.current, amount: 50, account: @account, merchant: @whole_foods_merchant)
+    transaction_entry2 = create_transaction(date: Date.current, amount: 100, account: @account, merchant: @whole_foods_merchant)
+
+    # Assign "Groceries" to transactions with a merchant of "Whole Foods" and an amount greater than $60
+    rule = Rule.create!(
+      family: @family,
+      resource_type: "transaction",
+      effective_date: 1.day.ago.to_date,
+      conditions: [
+        Rule::Condition.new(condition_type: "compound", operator: "and", sub_conditions: [
+          Rule::Condition.new(condition_type: "transaction_merchant", operator: "=", value: @whole_foods_merchant.id),
+          Rule::Condition.new(condition_type: "transaction_amount", operator: ">", value: 60)
+        ])
+      ],
+      actions: [ Rule::Action.new(action_type: "set_transaction_category", value: @groceries_category.id) ]
+    )
+
+    rule.apply
+
+    transaction_entry1.reload
+    transaction_entry2.reload
+
+    assert_nil transaction_entry1.transaction.category
+    assert_equal @groceries_category, transaction_entry2.transaction.category
+  end
+
+  # Artificial limitation put in place to prevent users from creating overly complex rules
+  # Rules should be shallow and wide
+  test "no nested compound conditions" do
+    rule = Rule.new(
+      family: @family,
+      resource_type: "transaction",
+      actions: [ Rule::Action.new(action_type: "set_transaction_category", value: @groceries_category.id) ],
+      conditions: [
+        Rule::Condition.new(condition_type: "compound", operator: "and", sub_conditions: [
+          Rule::Condition.new(condition_type: "compound", operator: "and", sub_conditions: [
+            Rule::Condition.new(condition_type: "transaction_name", operator: "=", value: "Starbucks")
+          ])
+        ])
+      ]
+    )
+
+    assert_not rule.valid?
+    assert_equal [ "Compound conditions cannot be nested" ], rule.errors.full_messages
+  end
+end
diff --git a/test/system/settings_test.rb b/test/system/settings_test.rb
index 0fe32c6b..233b8a42 100644
--- a/test/system/settings_test.rb
+++ b/test/system/settings_test.rb
@@ -10,7 +10,7 @@ class SettingsTest < ApplicationSystemTestCase
       [ "Accounts", accounts_path ],
       [ "Tags", tags_path ],
       [ "Categories", categories_path ],
-      [ "Merchants", merchants_path ],
+      [ "Merchants", family_merchants_path ],
       [ "Imports", imports_path ],
       [ "What's new", changelog_path ],
       [ "Feedback", feedback_path ]
diff --git a/test/vcr_cassettes/openai/auto_categorize.yml b/test/vcr_cassettes/openai/auto_categorize.yml
new file mode 100644
index 00000000..8bd186c0
--- /dev/null
+++ b/test/vcr_cassettes/openai/auto_categorize.yml
@@ -0,0 +1,194 @@
+---
+http_interactions:
+- request:
+    method: post
+    uri: https://api.openai.com/v1/responses
+    body:
+      encoding: UTF-8
+      string: '{"model":"gpt-4.1-mini","input":[{"role":"developer","content":"Here
+        are the user''s available categories in JSON format:\n\n```json\n[{\"id\":\"shopping_id\",\"name\":\"Shopping\",\"is_subcategory\":false,\"parent_id\":null,\"classification\":\"expense\"},{\"id\":\"subscriptions_id\",\"name\":\"Subscriptions\",\"is_subcategory\":true,\"parent_id\":null,\"classification\":\"expense\"},{\"id\":\"restaurants_id\",\"name\":\"Restaurants\",\"is_subcategory\":false,\"parent_id\":null,\"classification\":\"expense\"},{\"id\":\"fast_food_id\",\"name\":\"Fast
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+        the available categories to auto-categorize the following transactions:\n\n```json\n[{\"id\":\"1\",\"name\":\"McDonalds\",\"amount\":20,\"classification\":\"expense\",\"merchant\":\"McDonalds\",\"hint\":\"Fast
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diff --git a/test/vcr_cassettes/openai/auto_detect_merchants.yml b/test/vcr_cassettes/openai/auto_detect_merchants.yml
new file mode 100644
index 00000000..c8f4a67e
--- /dev/null
+++ b/test/vcr_cassettes/openai/auto_detect_merchants.yml
@@ -0,0 +1,203 @@
+---
+http_interactions:
+- request:
+    method: post
+    uri: https://api.openai.com/v1/responses
+    body:
+      encoding: UTF-8
+      string: '{"model":"gpt-4.1-mini","input":[{"role":"developer","content":"Here
+        are the user''s available merchants in JSON format:\n\n```json\n[{\"name\":\"Shooters\"}]\n```\n\nUse
+        BOTH your knowledge AND the user-generated merchants to auto-detect the following
+        transactions:\n\n```json\n[{\"id\":\"1\",\"name\":\"McDonalds\",\"amount\":20,\"classification\":\"expense\"},{\"id\":\"2\",\"name\":\"local
+        pub\",\"amount\":20,\"classification\":\"expense\"},{\"id\":\"3\",\"name\":\"WMT
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+        123 abc\",\"amount\":20,\"classification\":\"expense\"},{\"id\":\"5\",\"name\":\"chaseX1231\",\"amount\":2000,\"classification\":\"income\"},{\"id\":\"6\",\"name\":\"check
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+        name: \"Some Amazon purchases\"\n\nResult:\n- business_name: \"Amazon\"\n-
+        business_url: \"amazon.com\"\n```\n\nExample 2 (generic business):\n\n```\nTransaction
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