diff --git a/Gemfile.lock b/Gemfile.lock
index 813d69c1..32fb9a8e 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -121,7 +121,7 @@ GEM
     bindex (0.8.1)
     bootsnap (1.18.4)
       msgpack (~> 1.2)
-    brakeman (6.2.2)
+    brakeman (7.0.0)
       racc
     builder (3.3.0)
     capybara (3.40.0)
diff --git a/app/assets/stylesheets/application.tailwind.css b/app/assets/stylesheets/application.tailwind.css
index d9ea7d48..de0b8978 100644
--- a/app/assets/stylesheets/application.tailwind.css
+++ b/app/assets/stylesheets/application.tailwind.css
@@ -29,6 +29,11 @@
     @apply focus:opacity-100 focus:outline-none focus:ring-0;
     @apply placeholder-shown:opacity-50;
     @apply disabled:text-gray-400;
+    @apply text-ellipsis overflow-hidden whitespace-nowrap;
+  }
+
+  select.form-field__input {
+    @apply pr-8;
   }
 
   .form-field__radio {
@@ -51,10 +56,18 @@
     @apply border-alpha-black-200 checked:bg-gray-900 checked:ring-gray-900 focus:ring-gray-900 focus-visible:ring-gray-900 checked:hover:bg-gray-500;
   }
 
+  [type='checkbox'].maybe-checkbox--light:disabled {
+    @apply cursor-not-allowed opacity-80 bg-gray-50 border-gray-200 checked:bg-gray-400 checked:ring-gray-400;
+  }
+
   [type='checkbox'].maybe-checkbox--dark {
     @apply ring-gray-900 checked:text-white;
   }
 
+  [type='checkbox'].maybe-checkbox--dark:disabled {
+    @apply cursor-not-allowed opacity-80 ring-gray-600;
+  }
+
   [type='checkbox'].maybe-checkbox--dark:checked {
     background-image: url("data:image/svg+xml,%3csvg viewBox='0 0 16 16' fill='111827' xmlns='http://www.w3.org/2000/svg'%3e%3cpath d='M12.207 4.793a1 1 0 010 1.414l-5 5a1 1 0 01-1.414 0l-2-2a1 1 0 011.414-1.414L6.5 9.086l4.293-4.293a1 1 0 011.414 0z'/%3e%3c/svg%3e");
   }
diff --git a/app/controllers/account/transactions_controller.rb b/app/controllers/account/transactions_controller.rb
index 6784aac6..028fd5d0 100644
--- a/app/controllers/account/transactions_controller.rb
+++ b/app/controllers/account/transactions_controller.rb
@@ -21,24 +21,6 @@ class Account::TransactionsController < ApplicationController
     redirect_back_or_to transactions_url, notice: t(".success", count: updated)
   end
 
-  def mark_transfers
-    Current.family
-      .entries
-      .where(id: bulk_update_params[:entry_ids])
-           .mark_transfers!
-
-    redirect_back_or_to transactions_url, notice: t(".success")
-  end
-
-  def unmark_transfers
-    Current.family
-      .entries
-      .where(id: bulk_update_params[:entry_ids])
-           .update_all marked_as_transfer: false
-
-    redirect_back_or_to transactions_url, notice: t(".success")
-  end
-
   private
     def bulk_delete_params
       params.require(:bulk_delete).permit(entry_ids: [])
diff --git a/app/controllers/account/transfer_matches_controller.rb b/app/controllers/account/transfer_matches_controller.rb
new file mode 100644
index 00000000..b686c6c8
--- /dev/null
+++ b/app/controllers/account/transfer_matches_controller.rb
@@ -0,0 +1,56 @@
+class Account::TransferMatchesController < ApplicationController
+  before_action :set_entry
+
+  def new
+    @accounts = Current.family.accounts.alphabetically.where.not(id: @entry.account_id)
+    @transfer_match_candidates = @entry.transfer_match_candidates
+  end
+
+  def create
+    @transfer = build_transfer
+    @transfer.save!
+    @transfer.sync_account_later
+
+    redirect_back_or_to transactions_path, notice: t(".success")
+  end
+
+  private
+    def set_entry
+      @entry = Current.family.entries.find(params[:transaction_id])
+    end
+
+    def transfer_match_params
+      params.require(:transfer_match).permit(:method, :matched_entry_id, :target_account_id)
+    end
+
+    def build_transfer
+      if transfer_match_params[:method] == "new"
+        target_account = Current.family.accounts.find(transfer_match_params[:target_account_id])
+
+        missing_transaction = Account::Transaction.new(
+          entry: target_account.entries.build(
+            amount: @entry.amount * -1,
+            currency: @entry.currency,
+            date: @entry.date,
+            name: "Transfer to #{@entry.amount.negative? ? @entry.account.name : target_account.name}",
+          )
+        )
+
+        transfer = Transfer.find_or_initialize_by(
+          inflow_transaction: @entry.amount.positive? ? missing_transaction : @entry.account_transaction,
+          outflow_transaction: @entry.amount.positive? ? @entry.account_transaction : missing_transaction
+        )
+        transfer.status = "confirmed"
+        transfer
+      else
+        target_transaction = Current.family.entries.find(transfer_match_params[:matched_entry_id])
+
+        transfer = Transfer.find_or_initialize_by(
+          inflow_transaction: @entry.amount.negative? ? @entry.account_transaction : target_transaction.account_transaction,
+          outflow_transaction: @entry.amount.negative? ? target_transaction.account_transaction : @entry.account_transaction
+        )
+        transfer.status = "confirmed"
+        transfer
+      end
+    end
+end
diff --git a/app/controllers/account/transfers_controller.rb b/app/controllers/account/transfers_controller.rb
deleted file mode 100644
index 0aaac5c2..00000000
--- a/app/controllers/account/transfers_controller.rb
+++ /dev/null
@@ -1,61 +0,0 @@
-class Account::TransfersController < ApplicationController
-  layout :with_sidebar
-
-  before_action :set_transfer, only: %i[destroy show update]
-
-  def new
-    @transfer = Account::Transfer.new
-  end
-
-  def show
-  end
-
-  def create
-    from_account = Current.family.accounts.find(transfer_params[:from_account_id])
-    to_account = Current.family.accounts.find(transfer_params[:to_account_id])
-
-    @transfer = Account::Transfer.build_from_accounts from_account, to_account, \
-                                             date: transfer_params[:date],
-                                             amount: transfer_params[:amount].to_d
-
-    if @transfer.save
-      @transfer.entries.each(&:sync_account_later)
-      redirect_to transactions_path, notice: t(".success")
-    else
-      # TODO: this is not an ideal way to handle errors and should eventually be improved.
-      # See: https://github.com/hotwired/turbo-rails/pull/367
-      flash[:alert] = @transfer.errors.full_messages.to_sentence
-      redirect_to transactions_path
-    end
-  end
-
-  def update
-    @transfer.update_entries!(transfer_update_params)
-    redirect_back_or_to transactions_url, notice: t(".success")
-  end
-
-  def destroy
-    @transfer.destroy!
-    redirect_back_or_to transactions_url, notice: t(".success")
-  end
-
-  private
-
-    def set_transfer
-      record = Account::Transfer.find(params[:id])
-
-      unless record.entries.all? { |entry| Current.family.accounts.include?(entry.account) }
-        raise ActiveRecord::RecordNotFound
-      end
-
-      @transfer = record
-    end
-
-    def transfer_params
-      params.require(:account_transfer).permit(:from_account_id, :to_account_id, :amount, :date, :name, :excluded)
-    end
-
-    def transfer_update_params
-      params.require(:account_transfer).permit(:excluded, :notes)
-    end
-end
diff --git a/app/controllers/concerns/entryable_resource.rb b/app/controllers/concerns/entryable_resource.rb
index 918b32bb..e3b7365f 100644
--- a/app/controllers/concerns/entryable_resource.rb
+++ b/app/controllers/concerns/entryable_resource.rb
@@ -52,11 +52,14 @@ module EntryableResource
       respond_to do |format|
         format.html { redirect_back_or_to account_path(@entry.account), notice: t("account.entries.update.success") }
         format.turbo_stream do
-          render turbo_stream: turbo_stream.replace(
-            "header_account_entry_#{@entry.id}",
-            partial: "#{entryable_type.name.underscore.pluralize}/header",
-            locals: { entry: @entry }
-          )
+          render turbo_stream: [
+            turbo_stream.replace(
+              "header_account_entry_#{@entry.id}",
+              partial: "#{entryable_type.name.underscore.pluralize}/header",
+              locals: { entry: @entry }
+            ),
+            turbo_stream.replace("account_entry_#{@entry.id}", partial: "account/entries/entry", locals: { entry: @entry })
+          ]
         end
       end
     else
diff --git a/app/controllers/transactions_controller.rb b/app/controllers/transactions_controller.rb
index 664c3080..f20a3304 100644
--- a/app/controllers/transactions_controller.rb
+++ b/app/controllers/transactions_controller.rb
@@ -6,10 +6,15 @@ class TransactionsController < ApplicationController
     search_query = Current.family.transactions.search(@q).includes(:entryable).reverse_chronological
     @pagy, @transaction_entries = pagy(search_query, limit: params[:per_page] || "50")
 
+    totals_query = search_query.incomes_and_expenses
+    family_currency = Current.family.currency
+    count_with_transfers = search_query.count
+    count_without_transfers = totals_query.count
+
     @totals = {
-      count: search_query.select { |t| t.currency == Current.family.currency }.count,
-      income: search_query.income_total(Current.family.currency).abs,
-      expense: search_query.expense_total(Current.family.currency)
+      count: ((count_with_transfers - count_without_transfers) / 2) + count_without_transfers,
+      income: totals_query.income_total(family_currency).abs,
+      expense: totals_query.expense_total(family_currency)
     }
   end
 
diff --git a/app/controllers/transfers_controller.rb b/app/controllers/transfers_controller.rb
new file mode 100644
index 00000000..14c64422
--- /dev/null
+++ b/app/controllers/transfers_controller.rb
@@ -0,0 +1,66 @@
+class TransfersController < ApplicationController
+  layout :with_sidebar
+
+  before_action :set_transfer, only: %i[destroy show update]
+
+  def new
+    @transfer = Transfer.new
+  end
+
+  def show
+  end
+
+  def create
+    from_account = Current.family.accounts.find(transfer_params[:from_account_id])
+    to_account = Current.family.accounts.find(transfer_params[:to_account_id])
+
+    @transfer = Transfer.from_accounts(
+      from_account: from_account,
+      to_account: to_account,
+      date: transfer_params[:date],
+      amount: transfer_params[:amount].to_d
+    )
+
+    if @transfer.save
+      @transfer.sync_account_later
+
+      flash[:notice] = t(".success")
+
+      respond_to do |format|
+        format.html { redirect_back_or_to transactions_path }
+        redirect_target_url = request.referer || transactions_path
+        format.turbo_stream { render turbo_stream: turbo_stream.action(:redirect, redirect_target_url) }
+      end
+    else
+      render :new, status: :unprocessable_entity
+    end
+  end
+
+  def update
+    @transfer.update!(transfer_update_params)
+    respond_to do |format|
+      format.html { redirect_back_or_to transactions_url, notice: t(".success") }
+      format.turbo_stream
+    end
+  end
+
+  def destroy
+    @transfer.destroy!
+    redirect_back_or_to transactions_url, notice: t(".success")
+  end
+
+  private
+    def set_transfer
+      @transfer = Transfer.find(params[:id])
+
+      raise ActiveRecord::RecordNotFound unless @transfer.belongs_to_family?(Current.family)
+    end
+
+    def transfer_params
+      params.require(:transfer).permit(:from_account_id, :to_account_id, :amount, :date, :name, :excluded)
+    end
+
+    def transfer_update_params
+      params.require(:transfer).permit(:notes, :status)
+    end
+end
diff --git a/app/helpers/account/entries_helper.rb b/app/helpers/account/entries_helper.rb
index 359a241a..7fb8a6a1 100644
--- a/app/helpers/account/entries_helper.rb
+++ b/app/helpers/account/entries_helper.rb
@@ -3,10 +3,6 @@ module Account::EntriesHelper
     "account/entries/entryables/#{permitted_entryable_key(entry)}/#{relative_partial_path}"
   end
 
-  def unconfirmed_transfer?(entry)
-    entry.marked_as_transfer? && entry.transfer.nil?
-  end
-
   def transfer_entries(entries)
     transfers = entries.select { |e| e.transfer_id.present? }
     transfers.map(&:transfer).uniq
@@ -18,8 +14,19 @@ module Account::EntriesHelper
         yield grouped_entries
       end
 
+      next if content.blank?
+
       render partial: "account/entries/entry_group", locals: { date:, entries: grouped_entries, content:, selectable:, totals: }
-    end.join.html_safe
+    end.compact.join.html_safe
+  end
+
+  def entry_name_detailed(entry)
+    [
+      entry.date,
+      format_money(entry.amount_money),
+      entry.account.name,
+      entry.display_name
+    ].join(" • ")
   end
 
   private
diff --git a/app/helpers/account/transfers_helper.rb b/app/helpers/account/transfers_helper.rb
deleted file mode 100644
index ba7a95ae..00000000
--- a/app/helpers/account/transfers_helper.rb
+++ /dev/null
@@ -1,2 +0,0 @@
-module Account::TransfersHelper
-end
diff --git a/app/helpers/application_helper.rb b/app/helpers/application_helper.rb
index 85aca138..0bead33e 100644
--- a/app/helpers/application_helper.rb
+++ b/app/helpers/application_helper.rb
@@ -67,9 +67,9 @@ module ApplicationHelper
     render partial: "shared/drawer", locals: { content:, reload_on_close: }
   end
 
-  def disclosure(title, &block)
+  def disclosure(title, default_open: true, &block)
     content = capture &block
-    render partial: "shared/disclosure", locals: { title: title, content: content }
+    render partial: "shared/disclosure", locals: { title: title, content: content, open: default_open }
   end
 
   def sidebar_link_to(name, path, options = {})
diff --git a/app/helpers/categories_helper.rb b/app/helpers/categories_helper.rb
index c58713d4..9250f1d7 100644
--- a/app/helpers/categories_helper.rb
+++ b/app/helpers/categories_helper.rb
@@ -5,6 +5,24 @@ module CategoriesHelper
       color: Category::UNCATEGORIZED_COLOR
   end
 
+  def transfer_category
+    Category.new \
+      name: "⇄ Transfer",
+      color: Category::TRANSFER_COLOR
+  end
+
+  def payment_category
+    Category.new \
+      name: "→ Payment",
+      color: Category::PAYMENT_COLOR
+  end
+
+  def trade_category
+    Category.new \
+      name: "Trade",
+      color: Category::TRADE_COLOR
+  end
+
   def family_categories
     [ null_category ].concat(Current.family.categories.alphabetically)
   end
diff --git a/app/javascript/controllers/bulk_select_controller.js b/app/javascript/controllers/bulk_select_controller.js
index 023e97da..22b0a59a 100644
--- a/app/javascript/controllers/bulk_select_controller.js
+++ b/app/javascript/controllers/bulk_select_controller.js
@@ -99,7 +99,9 @@ export default class extends Controller {
   }
 
   _rowsForGroup(group) {
-    return this.rowTargets.filter((row) => group.contains(row));
+    return this.rowTargets.filter(
+      (row) => group.contains(row) && !row.disabled,
+    );
   }
 
   _addToSelection(idToAdd) {
@@ -115,7 +117,9 @@ export default class extends Controller {
   }
 
   _selectAll() {
-    this.selectedIdsValue = this.rowTargets.map((t) => t.dataset.id);
+    this.selectedIdsValue = this.rowTargets
+      .filter((t) => !t.disabled)
+      .map((t) => t.dataset.id);
   }
 
   _updateView = () => {
diff --git a/app/javascript/controllers/transfer_match_controller.js b/app/javascript/controllers/transfer_match_controller.js
new file mode 100644
index 00000000..eda4a90c
--- /dev/null
+++ b/app/javascript/controllers/transfer_match_controller.js
@@ -0,0 +1,16 @@
+import { Controller } from "@hotwired/stimulus";
+
+// Connects to data-controller="transfer-match"
+export default class extends Controller {
+  static targets = ["newSelect", "existingSelect"];
+
+  update(event) {
+    if (event.target.value === "new") {
+      this.newSelectTarget.classList.remove("hidden");
+      this.existingSelectTarget.classList.add("hidden");
+    } else {
+      this.newSelectTarget.classList.add("hidden");
+      this.existingSelectTarget.classList.remove("hidden");
+    }
+  }
+}
diff --git a/app/models/account/entry.rb b/app/models/account/entry.rb
index 8d6a8f40..b9fd5534 100644
--- a/app/models/account/entry.rb
+++ b/app/models/account/entry.rb
@@ -30,7 +30,15 @@ class Account::Entry < ApplicationRecord
     )
   }
 
-  scope :without_transfers, -> { where(marked_as_transfer: false) }
+  # All entries that are not part of a pending/approved transfer (rejected transfers count as normal entries, so are included)
+  scope :incomes_and_expenses, -> {
+    joins(
+      'LEFT JOIN transfers AS inflow_transfers ON inflow_transfers.inflow_transaction_id = account_entries.entryable_id
+       LEFT JOIN transfers AS outflow_transfers ON outflow_transfers.outflow_transaction_id = account_entries.entryable_id'
+    )
+    .where("(inflow_transfers.id IS NULL AND outflow_transfers.id IS NULL) OR inflow_transfers.status = 'rejected' OR outflow_transfers.status = 'rejected'")
+  }
+
   scope :with_converted_amount, ->(currency) {
     # Join with exchange rates to convert the amount to the given currency
     # If no rate is available, exclude the transaction from the results
@@ -59,6 +67,15 @@ class Account::Entry < ApplicationRecord
     enriched_name.presence || name
   end
 
+  def transfer_match_candidates
+    account.family.entries
+          .where.not(account_id: account_id)
+          .where.not(id: id)
+          .where(amount: -amount)
+          .where(currency: currency)
+          .where(date: (date - 4.days)..(date + 4.days))
+  end
+
   class << self
     def search(params)
       Account::EntrySearch.new(params).build_query(all)
@@ -98,13 +115,6 @@ class Account::Entry < ApplicationRecord
       select("*").from(rolling_totals).where("date >= ?", period.date_range.first)
     end
 
-    def mark_transfers!
-      update_all marked_as_transfer: true
-
-      # Attempt to "auto match" and save a transfer if 2 transactions selected
-      Account::Transfer.new(entries: all).save if all.count == 2
-    end
-
     def bulk_update!(bulk_update_params)
       bulk_attributes = {
         date: bulk_update_params[:date],
@@ -128,7 +138,7 @@ class Account::Entry < ApplicationRecord
     end
 
     def income_total(currency = "USD")
-      total = without_transfers.account_transactions.includes(:entryable)
+      total = account_transactions.includes(:entryable).incomes_and_expenses
         .where("account_entries.amount <= 0")
                        .map { |e| e.amount_money.exchange_to(currency, date: e.date, fallback_rate: 0) }
                        .sum
@@ -137,29 +147,12 @@ class Account::Entry < ApplicationRecord
     end
 
     def expense_total(currency = "USD")
-      total = without_transfers.account_transactions.includes(:entryable)
+      total = account_transactions.includes(:entryable).incomes_and_expenses
                        .where("account_entries.amount > 0")
                        .map { |e| e.amount_money.exchange_to(currency, date: e.date, fallback_rate: 0) }
                        .sum
 
       Money.new(total, currency)
     end
-
-    private
-      def entryable_search(params)
-        entryable_ids = []
-        entryable_search_performed = false
-
-        Account::Entryable::TYPES.map(&:constantize).each do |entryable|
-          next unless entryable.requires_search?(params)
-
-          entryable_search_performed = true
-          entryable_ids += entryable.search(params).pluck(:id)
-        end
-
-        return nil unless entryable_search_performed
-
-        entryable_ids
-      end
   end
 end
diff --git a/app/models/account/entry_search.rb b/app/models/account/entry_search.rb
index c561765b..962cb5c0 100644
--- a/app/models/account/entry_search.rb
+++ b/app/models/account/entry_search.rb
@@ -6,8 +6,8 @@ class Account::EntrySearch
   attribute :amount, :string
   attribute :amount_operator, :string
   attribute :types, :string
-  attribute :accounts, :string
-  attribute :account_ids, :string
+  attribute :accounts, array: true
+  attribute :account_ids, array: true
   attribute :start_date, :string
   attribute :end_date, :string
 
@@ -27,8 +27,6 @@ class Account::EntrySearch
     query = query.where("account_entries.date <= ?", end_date) if end_date.present?
 
     if types.present?
-      query = query.where(marked_as_transfer: false) unless types.include?("transfer")
-
       if types.include?("income") && !types.include?("expense")
         query = query.where("account_entries.amount < 0")
       elsif types.include?("expense") && !types.include?("income")
diff --git a/app/models/account/syncer.rb b/app/models/account/syncer.rb
index 5b2e4aba..27cd139d 100644
--- a/app/models/account/syncer.rb
+++ b/app/models/account/syncer.rb
@@ -5,6 +5,8 @@ class Account::Syncer
   end
 
   def run
+    Transfer.auto_match_for_account(account)
+
     holdings = sync_holdings
     balances = sync_balances(holdings)
     account.reload
diff --git a/app/models/account/trade_builder.rb b/app/models/account/trade_builder.rb
index e62947f7..8e0f9ad7 100644
--- a/app/models/account/trade_builder.rb
+++ b/app/models/account/trade_builder.rb
@@ -4,6 +4,13 @@ class Account::TradeBuilder
   attr_accessor :account, :date, :amount, :currency, :qty,
                 :price, :ticker, :type, :transfer_account_id
 
+  attr_reader :buildable
+
+  def initialize(attributes = {})
+    super
+    @buildable = set_buildable
+  end
+
   def save
     buildable.save
   end
@@ -17,7 +24,7 @@ class Account::TradeBuilder
   end
 
   private
-    def buildable
+    def set_buildable
       case type
       when "buy", "sell"
         build_trade
@@ -55,9 +62,9 @@ class Account::TradeBuilder
         from_account = type == "withdrawal" ? account : transfer_account
         to_account = type == "withdrawal" ? transfer_account : account
 
-        Account::Transfer.build_from_accounts(
-          from_account,
-          to_account,
+        Transfer.from_accounts(
+          from_account: from_account,
+          to_account: to_account,
           date: date,
           amount: signed_amount
         )
@@ -67,7 +74,6 @@ class Account::TradeBuilder
           date: date,
           amount: signed_amount,
           currency: currency,
-          marked_as_transfer: true,
           entryable: Account::Transaction.new
         )
       end
diff --git a/app/models/account/transaction.rb b/app/models/account/transaction.rb
index afe5a568..91fc0420 100644
--- a/app/models/account/transaction.rb
+++ b/app/models/account/transaction.rb
@@ -6,6 +6,9 @@ class Account::Transaction < ApplicationRecord
   has_many :taggings, as: :taggable, dependent: :destroy
   has_many :tags, through: :taggings
 
+  has_one :transfer_as_inflow, class_name: "Transfer", foreign_key: "inflow_transaction_id", dependent: :restrict_with_exception
+  has_one :transfer_as_outflow, class_name: "Transfer", foreign_key: "outflow_transaction_id", dependent: :restrict_with_exception
+
   accepts_nested_attributes_for :taggings, allow_destroy: true
 
   scope :active, -> { where(excluded: false) }
@@ -15,4 +18,12 @@ class Account::Transaction < ApplicationRecord
       Account::TransactionSearch.new(params).build_query(all)
     end
   end
+
+  def transfer
+    transfer_as_inflow || transfer_as_outflow
+  end
+
+  def transfer?
+    transfer.present? && transfer.status != "rejected"
+  end
 end
diff --git a/app/models/account/transaction_search.rb b/app/models/account/transaction_search.rb
index f61fae69..12884302 100644
--- a/app/models/account/transaction_search.rb
+++ b/app/models/account/transaction_search.rb
@@ -18,6 +18,11 @@ class Account::TransactionSearch
   def build_query(scope)
     query = scope
 
+    if types.present? && types.exclude?("transfer")
+      query = query.joins("LEFT JOIN transfers ON transfers.inflow_transaction_id = account_entries.id OR transfers.outflow_transaction_id = account_entries.id")
+        .where("transfers.id IS NULL")
+    end
+
     if categories.present?
       if categories.exclude?("Uncategorized")
         query = query
diff --git a/app/models/account/transfer.rb b/app/models/account/transfer.rb
deleted file mode 100644
index ea908413..00000000
--- a/app/models/account/transfer.rb
+++ /dev/null
@@ -1,113 +0,0 @@
-class Account::Transfer < ApplicationRecord
-  has_many :entries, dependent: :destroy
-
-  validate :net_zero_flows, if: :single_currency_transfer?
-  validate :transaction_count, :from_different_accounts, :all_transactions_marked
-
-  def date
-    outflow_transaction&.date
-  end
-
-  def amount_money
-    entries.first&.amount_money&.abs || Money.new(0)
-  end
-
-  def from_name
-    from_account&.name || I18n.t("account/transfer.from_fallback_name")
-  end
-
-  def to_name
-    to_account&.name || I18n.t("account/transfer.to_fallback_name")
-  end
-
-  def name
-    I18n.t("account/transfer.name", from_account: from_name, to_account: to_name)
-  end
-
-  def from_account
-    outflow_transaction&.account
-  end
-
-  def to_account
-    inflow_transaction&.account
-  end
-
-  def inflow_transaction
-    entries.find { |e| e.amount.negative? }
-  end
-
-  def outflow_transaction
-    entries.find { |e| e.amount.positive? }
-  end
-
-  def update_entries!(params)
-    transaction do
-      entries.each do |entry|
-        entry.update!(params)
-      end
-    end
-  end
-
-  def sync_account_later
-    entries.each(&:sync_account_later)
-  end
-
-  class << self
-    def build_from_accounts(from_account, to_account, date:, amount:)
-      outflow = from_account.entries.build \
-        amount: amount.abs,
-        currency: from_account.currency,
-        date: date,
-        name: "Transfer to #{to_account.name}",
-        marked_as_transfer: true,
-        entryable: Account::Transaction.new
-
-      # Attempt to convert the amount to the to_account's currency. If the conversion fails,
-      # use the original amount.
-      converted_amount = begin
-        Money.new(amount.abs, from_account.currency).exchange_to(to_account.currency)
-      rescue Money::ConversionError
-        Money.new(amount.abs, from_account.currency)
-      end
-
-      inflow = to_account.entries.build \
-        amount: converted_amount.amount * -1,
-        currency: converted_amount.currency.iso_code,
-        date: date,
-        name: "Transfer from #{from_account.name}",
-        marked_as_transfer: true,
-        entryable: Account::Transaction.new
-
-      new entries: [ outflow, inflow ]
-    end
-  end
-
-  private
-
-    def single_currency_transfer?
-      entries.map { |e| e.currency }.uniq.size == 1
-    end
-
-    def transaction_count
-      unless entries.size == 2
-        errors.add :entries, :must_have_exactly_2_entries
-      end
-    end
-
-    def from_different_accounts
-      accounts = entries.map { |e| e.account_id }.uniq
-      errors.add :entries, :must_be_from_different_accounts if accounts.size < entries.size
-    end
-
-    def net_zero_flows
-      unless entries.sum(&:amount).zero?
-        errors.add :entries, :must_have_an_inflow_and_outflow_that_net_to_zero
-      end
-    end
-
-    def all_transactions_marked
-      unless entries.all?(&:marked_as_transfer)
-        errors.add :entries, :must_be_marked_as_transfer
-      end
-    end
-end
diff --git a/app/models/category.rb b/app/models/category.rb
index 6f50070b..8d0c24b6 100644
--- a/app/models/category.rb
+++ b/app/models/category.rb
@@ -17,6 +17,9 @@ class Category < ApplicationRecord
   COLORS = %w[#e99537 #4da568 #6471eb #db5a54 #df4e92 #c44fe9 #eb5429 #61c9ea #805dee #6ad28a]
 
   UNCATEGORIZED_COLOR = "#737373"
+  TRANSFER_COLOR = "#444CE7"
+  PAYMENT_COLOR = "#db5a54"
+  TRADE_COLOR = "#e99537"
 
   class Group
     attr_reader :category, :subcategories
diff --git a/app/models/demo/generator.rb b/app/models/demo/generator.rb
index 8041dea6..2f65b9da 100644
--- a/app/models/demo/generator.rb
+++ b/app/models/demo/generator.rb
@@ -36,6 +36,8 @@ class Demo::Generator
       create_car_and_loan!
       create_other_accounts!
 
+      create_transfer_transactions!
+
       puts "accounts created"
       puts "Demo data loaded successfully!"
     end
@@ -49,12 +51,14 @@ class Demo::Generator
       family_id = "d99e3c6e-d513-4452-8f24-dc263f8528c0" # deterministic demo id
 
       family = Family.find_by(id: family_id)
+      Transfer.destroy_all
       family.destroy! if family
 
       Family.create!(id: family_id, name: "Demo Family", stripe_subscription_status: "active").tap(&:reload)
     end
 
     def clear_data!
+      Transfer.destroy_all
       InviteCode.destroy_all
       User.find_by_email("user@maybe.local")&.destroy
       ExchangeRate.destroy_all
@@ -177,6 +181,40 @@ class Demo::Generator
       end
     end
 
+    def create_transfer_transactions!
+      checking = family.accounts.find_by(name: "Chase Checking")
+      credit_card = family.accounts.find_by(name: "Chase Credit Card")
+      investment = family.accounts.find_by(name: "Robinhood")
+
+      create_transaction!(
+        account: checking,
+        date: 1.day.ago.to_date,
+        amount: 100,
+        name: "Credit Card Payment"
+      )
+
+      create_transaction!(
+        account: credit_card,
+        date: 1.day.ago.to_date,
+        amount: -100,
+        name: "Credit Card Payment"
+      )
+
+      create_transaction!(
+        account: checking,
+        date: 3.days.ago.to_date,
+        amount: 500,
+        name: "Transfer to investment"
+      )
+
+      create_transaction!(
+        account: investment,
+        date: 2.days.ago.to_date,
+        amount: -500,
+        name: "Transfer from checking"
+      )
+    end
+
     def load_securities!
       # Create an unknown security to simulate edge cases
       Security.create! ticker: "UNKNOWN", name: "Unknown Demo Stock", exchange_mic: "UNKNOWN"
diff --git a/app/models/family.rb b/app/models/family.rb
index 69ac5eb7..601692ed 100644
--- a/app/models/family.rb
+++ b/app/models/family.rb
@@ -82,7 +82,9 @@ class Family < ApplicationRecord
 
   def snapshot_account_transactions
     period = Period.last_30_days
-    results = accounts.active.joins(:entries)
+    results = accounts.active
+                      .joins(:entries)
+                      .joins("LEFT JOIN transfers ON (transfers.inflow_transaction_id = account_entries.entryable_id OR transfers.outflow_transaction_id = account_entries.entryable_id)")
                       .select(
                         "accounts.*",
                         "COALESCE(SUM(account_entries.amount) FILTER (WHERE account_entries.amount > 0), 0) AS spending",
@@ -90,8 +92,7 @@ class Family < ApplicationRecord
                       )
                       .where("account_entries.date >= ?", period.date_range.begin)
                       .where("account_entries.date <= ?", period.date_range.end)
-                      .where("account_entries.marked_as_transfer = ?", false)
-                      .where("account_entries.entryable_type = ?", "Account::Transaction")
+                      .where("transfers.id IS NULL")
                       .group("accounts.id")
                       .having("SUM(ABS(account_entries.amount)) > 0")
                       .to_a
@@ -110,9 +111,7 @@ class Family < ApplicationRecord
   end
 
   def snapshot_transactions
-    candidate_entries = entries.account_transactions.without_transfers.excluding(
-      entries.joins(:account).where(amount: ..0, accounts: { classification: Account.classifications[:liability] })
-    )
+    candidate_entries = entries.account_transactions.incomes_and_expenses
     rolling_totals = Account::Entry.daily_rolling_totals(candidate_entries, self.currency, period: Period.last_30_days)
 
     spending = []
diff --git a/app/models/plaid_account.rb b/app/models/plaid_account.rb
index 5772f821..1fdf40ee 100644
--- a/app/models/plaid_account.rb
+++ b/app/models/plaid_account.rb
@@ -89,7 +89,6 @@ class PlaidAccount < ApplicationRecord
         t.amount = plaid_txn.amount
         t.currency = plaid_txn.iso_currency_code
         t.date = plaid_txn.date
-        t.marked_as_transfer = transfer?(plaid_txn)
         t.entryable = Account::Transaction.new(
           category: get_category(plaid_txn.personal_finance_category.primary),
           merchant: get_merchant(plaid_txn.merchant_name)
diff --git a/app/models/plaid_investment_sync.rb b/app/models/plaid_investment_sync.rb
index fd207116..8c1d9805 100644
--- a/app/models/plaid_investment_sync.rb
+++ b/app/models/plaid_investment_sync.rb
@@ -31,7 +31,6 @@ class PlaidInvestmentSync
             t.amount = transaction.amount
             t.currency = transaction.iso_currency_code
             t.date = transaction.date
-            t.marked_as_transfer = transaction.subtype.in?(%w[deposit withdrawal])
             t.entryable = Account::Transaction.new
           end
         else
diff --git a/app/models/transfer.rb b/app/models/transfer.rb
new file mode 100644
index 00000000..265c516b
--- /dev/null
+++ b/app/models/transfer.rb
@@ -0,0 +1,139 @@
+class Transfer < ApplicationRecord
+  belongs_to :inflow_transaction, class_name: "Account::Transaction"
+  belongs_to :outflow_transaction, class_name: "Account::Transaction"
+
+  enum :status, { pending: "pending", confirmed: "confirmed", rejected: "rejected" }
+
+  validate :transfer_has_different_accounts
+  validate :transfer_has_opposite_amounts
+  validate :transfer_within_date_range
+
+  class << self
+    def from_accounts(from_account:, to_account:, date:, amount:)
+      # Attempt to convert the amount to the to_account's currency.
+      # If the conversion fails, use the original amount.
+      converted_amount = begin
+        Money.new(amount.abs, from_account.currency).exchange_to(to_account.currency)
+      rescue Money::ConversionError
+        Money.new(amount.abs, from_account.currency)
+      end
+
+      new(
+        inflow_transaction: Account::Transaction.new(
+          entry: to_account.entries.build(
+            amount: converted_amount.amount.abs * -1,
+            currency: converted_amount.currency.iso_code,
+            date: date,
+            name: "Transfer from #{from_account.name}",
+            entryable: Account::Transaction.new
+          )
+        ),
+        outflow_transaction: Account::Transaction.new(
+          entry: from_account.entries.build(
+            amount: amount.abs,
+            currency: from_account.currency,
+            date: date,
+            name: "Transfer to #{to_account.name}",
+            entryable: Account::Transaction.new
+          )
+        ),
+        status: "confirmed"
+      )
+    end
+
+    def auto_match_for_account(account)
+      matches = account.entries.account_transactions.joins("
+        JOIN account_entries ae2 ON
+          account_entries.amount = -ae2.amount AND
+          account_entries.currency = ae2.currency AND
+          account_entries.account_id <> ae2.account_id AND
+          ABS(account_entries.date - ae2.date) <= 4
+      ").select(
+        "account_entries.id",
+        "account_entries.entryable_id AS e1_entryable_id",
+        "ae2.entryable_id AS e2_entryable_id",
+        "account_entries.amount AS e1_amount",
+        "ae2.amount AS e2_amount"
+      )
+
+      Transfer.transaction do
+        matches.each do |match|
+          inflow = match.e1_amount.negative? ? match.e1_entryable_id : match.e2_entryable_id
+          outflow = match.e1_amount.negative? ? match.e2_entryable_id : match.e1_entryable_id
+
+          # Skip all rejected, or already matched transfers
+          next if Transfer.exists?(
+            inflow_transaction_id: inflow,
+            outflow_transaction_id: outflow
+          )
+
+          Transfer.create!(
+            inflow_transaction_id: inflow,
+            outflow_transaction_id: outflow
+          )
+        end
+      end
+    end
+  end
+
+  def sync_account_later
+    inflow_transaction.entry.sync_account_later
+    outflow_transaction.entry.sync_account_later
+  end
+
+  def belongs_to_family?(family)
+    family.transactions.include?(inflow_transaction)
+  end
+
+  def to_account
+    inflow_transaction.entry.account
+  end
+
+  def from_account
+    outflow_transaction.entry.account
+  end
+
+  def amount_abs
+    inflow_transaction.entry.amount_money.abs
+  end
+
+  def name
+    if payment?
+      I18n.t("transfer.payment_name", to_account: to_account.name)
+    else
+      I18n.t("transfer.name", to_account: to_account.name)
+    end
+  end
+
+  def payment?
+    to_account.liability?
+  end
+
+  private
+    def transfer_has_different_accounts
+      return unless inflow_transaction.present? && outflow_transaction.present?
+      errors.add(:base, :must_be_from_different_accounts) if inflow_transaction.entry.account == outflow_transaction.entry.account
+    end
+
+    def transfer_has_opposite_amounts
+      return unless inflow_transaction.present? && outflow_transaction.present?
+
+      inflow_amount = inflow_transaction.entry.amount
+      outflow_amount = outflow_transaction.entry.amount
+
+      if inflow_transaction.entry.currency == outflow_transaction.entry.currency
+        # For same currency, amounts must be exactly opposite
+        errors.add(:base, :must_have_opposite_amounts) if inflow_amount + outflow_amount != 0
+      else
+        # For different currencies, just check the signs are opposite
+        errors.add(:base, :must_have_opposite_amounts) unless inflow_amount.negative? && outflow_amount.positive?
+      end
+    end
+
+    def transfer_within_date_range
+      return unless inflow_transaction.present? && outflow_transaction.present?
+
+      date_diff = (inflow_transaction.entry.date - outflow_transaction.entry.date).abs
+      errors.add(:base, :must_be_within_date_range) if date_diff > 4
+    end
+end
diff --git a/app/views/account/entries/index.html.erb b/app/views/account/entries/index.html.erb
index 31197675..1ac6de61 100644
--- a/app/views/account/entries/index.html.erb
+++ b/app/views/account/entries/index.html.erb
@@ -84,7 +84,7 @@
           </div>
 
           <div class="p-4 bg-white rounded-bl-lg rounded-br-lg">
-            <%= render "pagination", pagy: @pagy, current_path: account_path(@account, page: params[:page]) %>
+            <%= render "pagination", pagy: @pagy, current_path: account_path(@account, page: params[:page], tab: params[:tab]) %>
           </div>
         </div>
       <% end %>
diff --git a/app/views/account/trades/_form.html.erb b/app/views/account/trades/_form.html.erb
index aaaf6900..c8dae4d3 100644
--- a/app/views/account/trades/_form.html.erb
+++ b/app/views/account/trades/_form.html.erb
@@ -22,7 +22,7 @@
       { label: t(".type"), selected: type },
       { data: {
           action: "trade-form#changeType",
-          trade_form_url_param: new_account_trade_path(account_id: entry.account_id),
+          trade_form_url_param: new_account_trade_path(account_id: entry.account&.id || entry.account_id),
           trade_form_key_param: "type",
         }} %>
 
diff --git a/app/views/account/trades/_trade.html.erb b/app/views/account/trades/_trade.html.erb
index 8c5c924e..517dc64d 100644
--- a/app/views/account/trades/_trade.html.erb
+++ b/app/views/account/trades/_trade.html.erb
@@ -3,7 +3,7 @@
 <% trade, account = entry.account_trade, entry.account %>
 
 <div class="grid grid-cols-12 items-center <%= entry.excluded ? "text-gray-400 bg-gray-25" : "text-gray-900" %> text-sm font-medium p-4">
-  <div class="col-span-8 flex items-center gap-4">
+  <div class="col-span-6 flex items-center gap-4">
     <% if selectable %>
       <%= check_box_tag dom_id(entry, "selection"),
                         class: "maybe-checkbox maybe-checkbox--light",
@@ -30,6 +30,10 @@
     </div>
   </div>
 
+  <div class="col-span-2 flex items-center">
+    <%= render "categories/badge", category: trade_category %>
+  </div>
+
   <div class="col-span-2 justify-self-end font-medium text-sm">
     <%= content_tag :p,
                     format_money(-entry.amount_money),
diff --git a/app/views/account/transactions/_form.html.erb b/app/views/account/transactions/_form.html.erb
index 47a0f01c..34e32236 100644
--- a/app/views/account/transactions/_form.html.erb
+++ b/app/views/account/transactions/_form.html.erb
@@ -8,7 +8,7 @@
     <fieldset class="bg-gray-50 rounded-lg p-1 grid grid-flow-col justify-stretch gap-x-2">
       <%= radio_tab_tag form: f, name: :nature, value: :outflow, label: t(".expense"), icon: "minus-circle", checked: params[:nature] == "outflow" || params[:nature].nil? %>
       <%= radio_tab_tag form: f, name: :nature, value: :inflow, label: t(".income"), icon: "plus-circle", checked: params[:nature] == "inflow" %>
-      <%= link_to new_account_transfer_path, data: { turbo_frame: :modal }, class: "flex px-4 py-1 rounded-lg items-center space-x-2 justify-center text-gray-400 group-has-[:checked]:bg-white group-has-[:checked]:text-gray-800 group-has-[:checked]:shadow-sm" do %>
+      <%= link_to new_transfer_path, data: { turbo_frame: :modal }, class: "flex px-4 py-1 rounded-lg items-center space-x-2 justify-center text-gray-400 group-has-[:checked]:bg-white group-has-[:checked]:text-gray-800 group-has-[:checked]:shadow-sm" do %>
         <%= lucide_icon "arrow-right-left", class: "w-5 h-5" %>
         <%= tag.span t(".transfer") %>
       <% end %>
diff --git a/app/views/account/transactions/_header.html.erb b/app/views/account/transactions/_header.html.erb
index af819326..401157f1 100644
--- a/app/views/account/transactions/_header.html.erb
+++ b/app/views/account/transactions/_header.html.erb
@@ -12,7 +12,7 @@
       </span>
     </h3>
 
-    <% if entry.marked_as_transfer? %>
+    <% if entry.account_transaction.transfer? %>
       <%= lucide_icon "arrow-left-right", class: "text-gray-500 mt-1 w-5 h-5" %>
     <% end %>
   </div>
diff --git a/app/views/account/transactions/_selection_bar.html.erb b/app/views/account/transactions/_selection_bar.html.erb
index 4fae27fa..1c38f869 100644
--- a/app/views/account/transactions/_selection_bar.html.erb
+++ b/app/views/account/transactions/_selection_bar.html.erb
@@ -8,26 +8,6 @@
   <div class="flex items-center gap-1 text-gray-500">
     <%= turbo_frame_tag "bulk_transaction_edit_drawer" %>
 
-    <%= form_with url: mark_transfers_account_transactions_path,
-                  scope: "bulk_update",
-                  data: {
-                    turbo_frame: "_top",
-                    turbo_confirm: {
-                      title: t(".mark_transfers"),
-                      body: t(".mark_transfers_message"),
-                      accept: t(".mark_transfers_confirm"),
-                    }
-                  } do |f| %>
-      <button id="bulk-transfer-btn"
-              type="button"
-              data-bulk-select-scope-param="bulk_update"
-              data-action="bulk-select#submitBulkRequest"
-              class="p-1.5 group hover:bg-gray-700 flex items-center justify-center rounded-md"
-              title="Mark as transfer">
-        <%= lucide_icon "arrow-right-left", class: "w-5 group-hover:text-white" %>
-      </button>
-    <% end %>
-
     <%= link_to bulk_edit_account_transactions_path,
                 class: "p-1.5 group hover:bg-gray-700 flex items-center justify-center rounded-md",
                 title: "Edit",
diff --git a/app/views/account/transactions/_transaction.html.erb b/app/views/account/transactions/_transaction.html.erb
index dfe0955a..6b963050 100644
--- a/app/views/account/transactions/_transaction.html.erb
+++ b/app/views/account/transactions/_transaction.html.erb
@@ -1,10 +1,11 @@
 <%# locals: (entry:, selectable: true, balance_trend: nil) %>
 <% transaction, account = entry.account_transaction, entry.account %>
 
-<div class="grid grid-cols-12 items-center <%= entry.excluded ? "text-gray-400 bg-gray-25" : "text-gray-900" %> text-sm font-medium p-4">
-  <div class="pr-10 flex items-center gap-4 col-span-6">
+<div class="grid grid-cols-12 items-center text-gray-900 text-sm font-medium p-4">
+  <div class="pr-10 flex items-center gap-4 <%= balance_trend ? "col-span-6" : "col-span-8" %>">
     <% if selectable %>
       <%= check_box_tag dom_id(entry, "selection"),
+                        disabled: entry.account_transaction.transfer?,
                         class: "maybe-checkbox maybe-checkbox--light",
                         data: { id: entry.id, "bulk-select-target": "row", action: "bulk-select#toggleRowSelection" } %>
     <% end %>
@@ -18,49 +19,44 @@
         <% end %>
 
         <div class="truncate">
-          <% if entry.new_record? %>
-            <%= content_tag :p, entry.display_name %>
-          <% else %>
-            <%= link_to entry.display_name,
-                        entry.transfer.present? ? account_transfer_path(entry.transfer) : account_entry_path(entry),
+          <div class="space-y-0.5">
+            <div class="flex items-center gap-1">
+              <% if entry.new_record? %>
+                <%= content_tag :p, entry.display_name %>
+              <% else %>
+                <%= link_to entry.display_name,
+                        entry.account_transaction.transfer? ? transfer_path(entry.account_transaction.transfer) : account_entry_path(entry),
                         data: { turbo_frame: "drawer", turbo_prefetch: false },
                         class: "hover:underline hover:text-gray-800" %>
-          <% end %>
+              <% end %>
+
+              <% if entry.excluded %>
+                <span title="One-time <%= entry.amount.negative? ? "income" : "expense" %> (excluded from averages)">
+                  <%= lucide_icon "asterisk", class: "w-4 h-4 shrink-0 text-orange-500" %>
+                </span>
+              <% end %>
+
+              <% if entry.account_transaction.transfer? %>
+                <%= render "account/transactions/transfer_match", entry: entry %>
+              <% end %>
+            </div>
+
+            <div class="text-gray-500 text-xs font-normal">
+              <% if entry.account_transaction.transfer? %>
+                <%= render "transfers/account_links", transfer: entry.account_transaction.transfer, is_inflow: entry.account_transaction.transfer_as_inflow.present? %>
+              <% else %>
+                <%= link_to entry.account.name, account_path(entry.account, tab: "transactions"), data: { turbo_frame: "_top" }, class: "hover:underline" %>
+              <% end %>
+            </div>
+          </div>
         </div>
       <% end %>
     </div>
-
-    <% if unconfirmed_transfer?(entry) %>
-      <%= render "account/transfers/transfer_toggle", entry: entry %>
-    <% end %>
   </div>
 
-  <% if entry.transfer.present? %>
-    <% unless balance_trend %>
-      <div class="col-span-2"></div>
-    <% end %>
-
-    <div class="col-span-2">
-      <%= render "account/transfers/account_logos", transfer: entry.transfer, outflow: entry.amount.positive? %>
-    </div>
-  <% else %>
-    <div class="flex items-center gap-1 col-span-2">
-      <%= render "categories/menu", transaction: transaction %>
-    </div>
-
-    <% unless balance_trend %>
-      <%= tag.div class: "col-span-2 overflow-hidden truncate" do %>
-        <% if entry.new_record? %>
-          <%= tag.p account.name %>
-        <% else %>
-          <%= link_to account.name,
-                      account_path(account, tab: "transactions"),
-                      data: { turbo_frame: "_top" },
-                      class: "hover:underline" %>
-        <% end %>
-      <% end %>
-    <% end %>
-  <% end %>
+  <div class="flex items-center gap-1 col-span-2">
+    <%= render "account/transactions/transaction_category", entry: entry %>
+  </div>
 
   <div class="col-span-2 ml-auto">
     <%= content_tag :p,
diff --git a/app/views/account/transactions/_transaction_category.html.erb b/app/views/account/transactions/_transaction_category.html.erb
new file mode 100644
index 00000000..ab0b33c8
--- /dev/null
+++ b/app/views/account/transactions/_transaction_category.html.erb
@@ -0,0 +1,9 @@
+<%# locals: (entry:) %>
+
+<div id="<%= dom_id(entry, "category_menu") %>">
+  <% if entry.account_transaction.transfer? %>
+    <%= render "categories/badge", category: entry.account_transaction.transfer.payment? ? payment_category : transfer_category %>
+  <% else %>
+    <%= render "categories/menu", transaction: entry.account_transaction %>
+  <% end %>
+</div>
diff --git a/app/views/account/transactions/_transfer_match.html.erb b/app/views/account/transactions/_transfer_match.html.erb
new file mode 100644
index 00000000..7175e02e
--- /dev/null
+++ b/app/views/account/transactions/_transfer_match.html.erb
@@ -0,0 +1,27 @@
+<%# locals: (entry:) %>
+
+<div id="<%= dom_id(entry, "transfer_match") %>" class="flex items-center gap-1">
+  <% if entry.account_transaction.transfer.confirmed? %>
+    <span title="<%= entry.account_transaction.transfer.payment? ? "Payment" : "Transfer" %> is confirmed">
+      <%= lucide_icon "link-2", class: "w-4 h-4 text-indigo-600" %>
+    </span>
+  <% elsif entry.account_transaction.transfer.pending? %>
+    <span class="inline-flex items-center rounded-full bg-indigo-50 px-2 py-0.5 text-xs font-medium text-indigo-700">
+      Auto-matched
+    </span>
+
+    <%= button_to transfer_path(entry.account_transaction.transfer, transfer: { status: "confirmed" }),
+                    method: :patch,
+                    class: "text-gray-500 hover:text-gray-800 flex items-center justify-center",
+                    title: "Confirm match" do %>
+      <%= lucide_icon "check", class: "w-4 h-4 text-indigo-400 hover:text-indigo-600" %>
+    <% end %>
+
+    <%= button_to transfer_path(entry.account_transaction.transfer, transfer: { status: "rejected" }),
+                    method: :patch,
+                    class: "text-gray-500 hover:text-gray-800 flex items-center justify-center",
+                    title: "Reject match" do %>
+      <%= lucide_icon "x", class: "w-4 h-4 text-gray-400 hover:text-gray-600" %>
+    <% end %>
+  <% end %>
+</div>
diff --git a/app/views/account/transactions/show.html.erb b/app/views/account/transactions/show.html.erb
index b512b43a..5658bd65 100644
--- a/app/views/account/transactions/show.html.erb
+++ b/app/views/account/transactions/show.html.erb
@@ -19,7 +19,7 @@
                 max: Date.current,
                 "data-auto-submit-form-target": "auto" %>
 
-          <% unless @entry.marked_as_transfer? %>
+          <% unless @entry.account_transaction.transfer? %>
             <div class="flex items-center gap-2">
               <%= f.select :nature,
                     [["Expense", "outflow"], ["Income", "inflow"]],
@@ -32,27 +32,7 @@
                     min: 0,
                     value: @entry.amount.abs %>
             </div>
-          <% end %>
 
-          <%= f.select :account,
-                options_for_select(
-                  Current.family.accounts.alphabetically.pluck(:name, :id),
-                  @entry.account_id
-                ),
-                { label: t(".account_label") },
-                { disabled: true } %>
-        <% end %>
-      </div>
-    <% end %>
-
-    <!-- Details Section -->
-    <%= disclosure t(".details") do %>
-      <div class="pb-4">
-        <%= styled_form_with model: @entry,
-              url: account_transaction_path(@entry),
-              class: "space-y-2",
-              data: { controller: "auto-submit-form" } do |f| %>
-          <% unless @entry.marked_as_transfer? %>
             <%= f.fields_for :entryable do |ef| %>
               <%= ef.collection_select :category_id,
                       Current.family.categories.alphabetically,
@@ -60,6 +40,30 @@
                     { label: t(".category_label"),
                       class: "text-gray-400", include_blank: t(".uncategorized") },
                     "data-auto-submit-form-target": "auto" %>
+            <% end %>
+          <% end %>
+
+        <% end %>
+      </div>
+    <% end %>
+
+    <!-- Details Section -->
+    <%= disclosure t(".details"), default_open: false do %>
+      <div class="pb-4">
+        <%= styled_form_with model: @entry,
+              url: account_transaction_path(@entry),
+              class: "space-y-2",
+              data: { controller: "auto-submit-form" } do |f| %>
+          <% unless @entry.account_transaction.transfer? %>
+            <%= f.select :account,
+                options_for_select(
+                  Current.family.accounts.alphabetically.pluck(:name, :id),
+                  @entry.account_id
+                ),
+                { label: t(".account_label") },
+                { disabled: true } %>
+
+            <%= f.fields_for :entryable do |ef| %>
 
               <%= ef.collection_select :merchant_id,
                       Current.family.merchants.alphabetically,
@@ -94,15 +98,15 @@
     <!-- Settings Section -->
     <%= disclosure t(".settings") do %>
       <div class="pb-4">
-        <!-- Exclude Transaction Form -->
+
         <%= styled_form_with model: @entry,
               url: account_transaction_path(@entry),
               class: "p-3",
               data: { controller: "auto-submit-form" } do |f| %>
-          <div class="flex cursor-pointer items-center gap-2 justify-between">
+          <div class="flex cursor-pointer items-center gap-4 justify-between">
             <div class="text-sm space-y-1">
-              <h4 class="text-gray-900"><%= t(".exclude_title") %></h4>
-              <p class="text-gray-500"><%= t(".exclude_subtitle") %></p>
+              <h4 class="text-gray-900">One-time <%= @entry.amount.negative? ? "Income" : "Expense" %></h4>
+              <p class="text-gray-500">One-time transactions will be excluded from certain budgeting calculations and reports to help you see what's really important.</p>
             </div>
 
             <div class="relative inline-block select-none">
@@ -115,6 +119,18 @@
           </div>
         <% end %>
 
+        <div class="flex items-center justify-between gap-4 p-3">
+          <div class="text-sm space-y-1">
+            <h4 class="text-gray-900">Transfer or Debt Payment?</h4>
+            <p class="text-gray-500">Transfers and payments are special types of transactions that indicate money movement between 2 accounts.</p>
+          </div>
+
+          <%= link_to new_account_transaction_transfer_match_path(@entry), class: "btn btn--outline flex items-center gap-2", data: { turbo_frame: :modal } do %>
+            <%= lucide_icon "arrow-left-right", class: "w-4 h-4 shrink-0" %>
+            <span class="whitespace-nowrap">Open matcher</span>
+          <% end %>
+        </div>
+
         <!-- Delete Transaction Form -->
         <div class="flex items-center justify-between gap-2 p-3">
           <div class="text-sm space-y-1">
diff --git a/app/views/account/transfer_matches/_matching_fields.html.erb b/app/views/account/transfer_matches/_matching_fields.html.erb
new file mode 100644
index 00000000..cc087123
--- /dev/null
+++ b/app/views/account/transfer_matches/_matching_fields.html.erb
@@ -0,0 +1,44 @@
+<%# locals: (form:, entry:, candidates:, accounts:) %>
+
+<% if candidates.any? %>
+  <div data-controller="transfer-match" class="space-y-2">
+    <p class="text-sm text-gray-500">
+      Select a method for matching your transactions.
+    </p>
+
+    <%= form.select :method,
+              [
+                ["Match existing transaction (recommended)", "existing"],
+                ["Create new transaction", "new"]
+              ],
+              { selected: "existing", label: "Matching method" },
+              data: { action: "change->transfer-match#update" } %>
+
+    <div data-transfer-match-target="existingSelect">
+      <%= form.select :matched_entry_id,
+                candidates.map { |entry|
+                  [entry_name_detailed(entry), entry.id]
+                },
+                { label: "Matching transaction" } %>
+    </div>
+
+    <div data-transfer-match-target="newSelect" class="hidden">
+      <%= form.select :target_account_id,
+                accounts.map { |account| [account.name, account.id] },
+                { label: "Target account" } %>
+    </div>
+  </div>
+<% else %>
+  <p class="text-sm text-gray-500">
+    We couldn't find any transactions to match from your other accounts.
+    Please select an account and we will create a new inflow transaction for you.
+  </p>
+
+  <%= form.hidden_field :method, value: "new" %>
+
+  <div>
+    <%= form.select :target_account_id,
+                accounts.map { |account| [account.name, account.id] },
+                { label: "Target account" } %>
+  </div>
+<% end %>
diff --git a/app/views/account/transfer_matches/new.html.erb b/app/views/account/transfer_matches/new.html.erb
new file mode 100644
index 00000000..49a450bf
--- /dev/null
+++ b/app/views/account/transfer_matches/new.html.erb
@@ -0,0 +1,60 @@
+<%= modal_form_wrapper title: "Match transfer or payment" do %>
+  <%= styled_form_with(
+        url: account_transaction_transfer_match_path(@entry),
+        scope: :transfer_match,
+        class: "space-y-8",
+        data: { turbo_frame: :_top }
+      ) do |f| %>
+    <section class="space-y-4">
+      <div class="space-y-2">
+        <h2 class="text-sm font-medium text-gray-700">
+          <%= @entry.amount.positive? ? "From account: #{@entry.account.name}" : "From account" %>
+        </h2>
+
+        <% if @entry.amount.positive? %>
+          <%= f.select(
+                :entry_id,
+                [[entry_name_detailed(@entry), @entry.id]],
+                {
+                  label: "Outflow transaction",
+                  selected: @entry.id,
+                },
+                disabled: true
+              ) %>
+        <% else %>
+          <%= render "account/transfer_matches/matching_fields",
+                      form: f, entry: @entry, candidates: @transfer_match_candidates, accounts: @accounts %>
+        <% end %>
+      </div>
+    </section>
+
+    <div class="flex justify-center py-2">
+      <%= lucide_icon "arrow-down", class: "w-5 h-5" %>
+    </div>
+
+    <section class="space-y-4">
+      <div class="space-y-2">
+        <h2 class="text-sm font-medium text-gray-700">
+          <%= @entry.amount.negative? ? "To account: #{@entry.account.name}" : "To account" %>
+        </h2>
+
+        <% if @entry.amount.negative? %>
+          <%= f.select(
+                :entry_id,
+                [[entry_name_detailed(@entry), @entry.id]],
+                {
+                  label: "Inflow transaction",
+                  selected: @entry.id,
+                },
+                disabled: true
+              ) %>
+        <% else %>
+          <%= render "account/transfer_matches/matching_fields",
+                      form: f, entry: @entry, candidates: @transfer_match_candidates, accounts: @accounts %>
+        <% end %>
+      </div>
+    </section>
+
+    <%= f.submit "Create transfer match", data: { turbo_submits_with: "Saving..."} %>
+  <% end %>
+<% end %>
diff --git a/app/views/account/transfers/_account_logos.html.erb b/app/views/account/transfers/_account_logos.html.erb
deleted file mode 100644
index 2d668e33..00000000
--- a/app/views/account/transfers/_account_logos.html.erb
+++ /dev/null
@@ -1,25 +0,0 @@
-<%# locals: (transfer:, outflow: false) %>
-
-<div class="flex items-center gap-2">
-  <% if outflow %>
-    <%= link_to transfer.from_account, data: { turbo_frame: :_top }, class: "hover:opacity-90" do %>
-      <%= circle_logo(transfer.from_name[0].upcase, size: "sm") %>
-    <% end %>
-
-    <%= lucide_icon "arrow-right", class: "text-gray-500 w-4 h-4" %>
-
-    <%= link_to transfer.to_account, data: { turbo_frame: :_top }, class: "hover:opacity-90" do %>
-      <%= circle_logo(transfer.to_name[0].upcase, size: "sm") %>
-    <% end %>
-  <% else %>
-    <%= link_to transfer.to_account, data: { turbo_frame: :_top }, class: "hover:opacity-90" do %>
-      <%= circle_logo(transfer.to_name[0].upcase, size: "sm") %>
-    <% end %>
-
-    <%= lucide_icon "arrow-left", class: "text-gray-500 w-4 h-4" %>
-
-    <%= link_to transfer.from_account, data: { turbo_frame: :_top }, class: "hover:opacity-90" do %>
-      <%= circle_logo(transfer.from_name[0].upcase, size: "sm") %>
-    <% end %>
-  <% end %>
-</div>
diff --git a/app/views/account/transfers/_transfer_toggle.html.erb b/app/views/account/transfers/_transfer_toggle.html.erb
deleted file mode 100644
index 233b11e7..00000000
--- a/app/views/account/transfers/_transfer_toggle.html.erb
+++ /dev/null
@@ -1,16 +0,0 @@
-<%# locals: (entry:) %>
-
-<%= form_with url: unmark_transfers_account_transactions_path, class: "flex items-center", data: {
-          turbo_confirm: {
-            title: t(".remove_transfer"),
-            body: t(".remove_transfer_body"),
-            accept: t(".remove_transfer_confirm"),
-          },
-          turbo_frame: "_top"
-        } do |f| %>
-  <%= f.hidden_field "bulk_update[entry_ids][]", value: entry.id %>
-  <%= f.button class: "flex items-center justify-center group", title: "Remove transfer" do %>
-    <%= lucide_icon "arrow-left-right", class: "group-hover:hidden text-gray-500 w-4 h-4" %>
-    <%= lucide_icon "unlink", class: "hidden group-hover:inline-block text-gray-900 w-4 h-4" %>
-  <% end %>
-<% end %>
diff --git a/app/views/account/valuations/_valuation.html.erb b/app/views/account/valuations/_valuation.html.erb
index 3e34cfba..fb74b750 100644
--- a/app/views/account/valuations/_valuation.html.erb
+++ b/app/views/account/valuations/_valuation.html.erb
@@ -12,7 +12,7 @@
     <% end %>
 
     <div class="flex items-center gap-3">
-      <%= tag.div class: "w-8 h-8 rounded-full p-1.5 flex items-center justify-center", style: mixed_hex_styles(color) do %>
+      <%= tag.div class: "w-6 h-6 rounded-full p-1.5 flex items-center justify-center", style: mixed_hex_styles(color) do %>
         <%= lucide_icon icon, class: "w-4 h-4" %>
       <% end %>
 
diff --git a/app/views/accounts/show/_activity.html.erb b/app/views/accounts/show/_activity.html.erb
index 290c5be5..86dc7038 100644
--- a/app/views/accounts/show/_activity.html.erb
+++ b/app/views/accounts/show/_activity.html.erb
@@ -1,5 +1,5 @@
 <%# locals: (account:) %>
 
-<%= turbo_frame_tag dom_id(account, :entries), src: account_entries_path(account_id: account.id, page: params[:page]) do %>
+<%= turbo_frame_tag dom_id(account, :entries), src: account_entries_path(account_id: account.id, page: params[:page], tab: params[:tab]) do %>
   <%= render "account/entries/loading" %>
 <% end %>
diff --git a/app/views/application/_pagination.html.erb b/app/views/application/_pagination.html.erb
index f4548512..13da2cd9 100644
--- a/app/views/application/_pagination.html.erb
+++ b/app/views/application/_pagination.html.erb
@@ -3,7 +3,7 @@
   <div class="flex items-center gap-1">
     <div>
       <% if pagy.prev %>
-        <%= link_to custom_pagy_url_for(pagy, pagy.prev, current_path: current_path), 
+        <%= link_to custom_pagy_url_for(pagy, pagy.prev, current_path: current_path),
               class: "inline-flex items-center p-2 text-sm font-medium text-gray-500 hover:border-gray-300 hover:text-gray-700",
               data: (current_path ? { turbo_frame: "_top" } : {}) do %>
           <%= lucide_icon("chevron-left", class: "w-5 h-5 text-gray-500") %>
@@ -17,13 +17,13 @@
     <div class="rounded-xl p-1 bg-gray-25">
       <% pagy.series.each do |series_item| %>
         <% if series_item.is_a?(Integer) %>
-          <%= link_to custom_pagy_url_for(pagy, series_item, current_path: current_path), 
+          <%= link_to custom_pagy_url_for(pagy, series_item, current_path: current_path),
                 class: "rounded-md px-2 py-1 inline-flex items-center text-sm font-medium text-gray-500 hover:border-gray-300 hover:text-gray-700",
                 data: (current_path ? { turbo_frame: "_top" } : {}) do %>
             <%= series_item %>
           <% end %>
         <% elsif series_item.is_a?(String) %>
-          <%= link_to custom_pagy_url_for(pagy, series_item, current_path: current_path), 
+          <%= link_to custom_pagy_url_for(pagy, series_item, current_path: current_path),
                 class: "rounded-md px-2 py-1 bg-white border border-alpha-black-25 shadow-xs inline-flex items-center text-sm font-medium text-gray-900",
                 data: (current_path ? { turbo_frame: "_top" } : {}) do %>
             <%= series_item %>
@@ -35,7 +35,7 @@
     </div>
     <div>
       <% if pagy.next %>
-        <%= link_to custom_pagy_url_for(pagy, pagy.next, current_path: current_path), 
+        <%= link_to custom_pagy_url_for(pagy, pagy.next, current_path: current_path),
               class: "inline-flex items-center p-2 text-sm font-medium text-gray-500 hover:border-gray-300 hover:text-gray-700",
               data: (current_path ? { turbo_frame: "_top" } : {}) do %>
           <%= lucide_icon("chevron-right", class: "w-5 h-5 text-gray-500") %>
diff --git a/app/views/categories/_badge.html.erb b/app/views/categories/_badge.html.erb
index 1b4c399b..b6c6480c 100644
--- a/app/views/categories/_badge.html.erb
+++ b/app/views/categories/_badge.html.erb
@@ -9,4 +9,5 @@
           color: <%= category.color %>;">
     <%= category.name %>
   </span>
+
 </div>
diff --git a/app/views/category/dropdowns/show.html.erb b/app/views/category/dropdowns/show.html.erb
index 082cd836..6df124ee 100644
--- a/app/views/category/dropdowns/show.html.erb
+++ b/app/views/category/dropdowns/show.html.erb
@@ -29,16 +29,8 @@
     </div>
     <hr>
     <div class="relative p-1.5 w-full">
-      <%= link_to new_category_path(transaction_id: @transaction),
-                  class: "flex text-sm font-medium items-center gap-2 text-gray-500 w-full rounded-lg p-2 hover:bg-gray-100",
-                  data: { turbo_frame: "modal" } do %>
-        <%= lucide_icon "plus", class: "w-5 h-5" %>
-
-        <%= t(".add_new") %>
-      <% end %>
-
       <% if @transaction.category %>
-        <%= button_to account_transaction_path(@transaction.entry.account, @transaction.entry),
+        <%= button_to account_transaction_path(@transaction.entry),
                       method: :patch,
                       data: { turbo_frame: dom_id(@transaction.entry) },
                       params: { account_entry: { entryable_type: "Account::Transaction", entryable_attributes: { id: @transaction.id, category_id: nil } } },
@@ -48,6 +40,32 @@
           <%= t(".clear") %>
         <% end %>
       <% end %>
+
+      <%= link_to new_account_transaction_transfer_match_path(@transaction.entry),
+                  class: "flex text-sm font-medium items-center gap-2 text-gray-500 w-full rounded-lg p-2 hover:bg-gray-100",
+                  data: { turbo_frame: "modal" } do %>
+        <%= lucide_icon "refresh-cw", class: "w-5 h-5" %>
+
+        <p>Match transfer/payment</p>
+      <% end %>
+
+      <div class="flex text-sm font-medium items-center gap-2 text-gray-500 w-full rounded-lg p-2">
+        <div class="flex items-center gap-2">
+          <%= form_with url: account_transaction_path(@transaction.entry),
+                        method: :patch,
+                        data: { controller: "auto-submit-form" } do |f| %>
+            <%= f.hidden_field "account_entry[excluded]", value: !@transaction.entry.excluded %>
+            <%= f.check_box "account_entry[excluded]",
+                          checked: @transaction.entry.excluded,
+                          class: "maybe-checkbox maybe-checkbox--light",
+                          data: { auto_submit_form_target: "auto", autosubmit_trigger_event: "change" } %>
+          <% end %>
+        </div>
+
+        <p>One-time <%= @transaction.entry.amount.negative? ? "income" : "expense" %></p>
+
+        <%= lucide_icon "asterisk", class: "w-5 h-5 shrink-0 text-orange-500 ml-auto" %>
+      </div>
     </div>
   </div>
 <% end %>
diff --git a/app/views/pages/early_access.html.erb b/app/views/pages/early_access.html.erb
index 6ec820e1..cd86b0c3 100644
--- a/app/views/pages/early_access.html.erb
+++ b/app/views/pages/early_access.html.erb
@@ -10,7 +10,6 @@
     <%= stylesheet_link_tag "application", "data-turbo-track": "reload" %>
 
     <%= javascript_importmap_tags %>
-    <%= hotwire_livereload_tags if Rails.env.development? %>
     <%= turbo_refreshes_with method: :morph, scroll: :preserve %>
 
     <meta name="viewport" content="viewport-fit=cover, width=device-width, initial-scale=1.0, minimum-scale=1.0, maximum-scale=1.0, user-scalable=no">
diff --git a/app/views/shared/_modal_form.html.erb b/app/views/shared/_modal_form.html.erb
index e0e69e01..11b8d26a 100644
--- a/app/views/shared/_modal_form.html.erb
+++ b/app/views/shared/_modal_form.html.erb
@@ -1,7 +1,7 @@
 <%# locals: (title:, content:, subtitle: nil) %>
 
 <%= modal do %>
-  <article class="mx-auto w-full p-4 space-y-4 min-w-[450px] max-w-xl">
+  <article class="mx-auto w-full p-4 space-y-4 min-w-[450px]">
     <div class="space-y-2">
       <header class="flex justify-between items-center">
         <h2 class="font-medium"><%= title %></h2>
diff --git a/app/views/transactions/index.html.erb b/app/views/transactions/index.html.erb
index 4008af8e..37d82f29 100644
--- a/app/views/transactions/index.html.erb
+++ b/app/views/transactions/index.html.erb
@@ -17,20 +17,24 @@
     <% if @transaction_entries.present? %>
       <div class="grow overflow-y-auto">
         <div class="grid grid-cols-12 bg-gray-25 rounded-xl px-5 py-3 text-xs uppercase font-medium text-gray-500 items-center mb-4">
-          <div class="pl-0.5 col-span-6 flex items-center gap-4">
+          <div class="pl-0.5 col-span-8 flex items-center gap-4">
             <%= check_box_tag "selection_entry",
                               class: "maybe-checkbox maybe-checkbox--light",
                               data: { action: "bulk-select#togglePageSelection" } %>
-            <p class="col-span-4">transaction</p>
+            <p>transaction</p>
           </div>
 
           <p class="col-span-2">category</p>
-          <p class="col-span-2">account</p>
           <p class="col-span-2 justify-self-end">amount</p>
         </div>
         <div class="space-y-6">
           <%= entries_by_date(@transaction_entries, totals: true) do |entries| %>
-            <%= render entries %>
+            <%# Render transfers by selecting one side of the transfer (to prevent double-rendering the same transfer across date groups) %>
+            <%= render partial: "transfers/transfer",
+                       collection: entries.select { |e| e.account_transaction.transfer? && e.account_transaction.transfer_as_outflow.present? }.map { |e| e.account_transaction.transfer_as_outflow } %>
+
+            <%# Render regular entries %>
+            <%= render partial: "account/entries/entry", collection: entries.reject { |e| e.account_transaction.transfer? } %>
           <% end %>
         </div>
       </div>
diff --git a/app/views/transfers/_account_links.html.erb b/app/views/transfers/_account_links.html.erb
new file mode 100644
index 00000000..a71b7de0
--- /dev/null
+++ b/app/views/transfers/_account_links.html.erb
@@ -0,0 +1,7 @@
+<%# locals: (transfer:, is_inflow: false) %>
+<div class="flex items-center gap-1">
+  <% first_account, second_account = is_inflow ? [transfer.to_account, transfer.from_account] : [transfer.from_account, transfer.to_account] %>
+  <%= link_to first_account.name, account_path(first_account, tab: "activity"), class: "hover:underline", data: { turbo_frame: "_top" } %>
+  <%= lucide_icon is_inflow ? "arrow-left" : "arrow-right", class: "w-4 h-4 shrink-0" %>
+  <%= link_to second_account.name, account_path(second_account, tab: "activity"), class: "hover:underline", data: { turbo_frame: "_top" } %>
+</div>
diff --git a/app/views/account/transfers/_form.html.erb b/app/views/transfers/_form.html.erb
similarity index 92%
rename from app/views/account/transfers/_form.html.erb
rename to app/views/transfers/_form.html.erb
index b55544a7..a08cbcae 100644
--- a/app/views/account/transfers/_form.html.erb
+++ b/app/views/transfers/_form.html.erb
@@ -29,7 +29,7 @@
     <%= f.collection_select :from_account_id, Current.family.accounts.manual.alphabetically, :id, :name, { prompt: t(".select_account"), label: t(".from") }, required: true %>
     <%= f.collection_select :to_account_id, Current.family.accounts.manual.alphabetically, :id, :name, { prompt: t(".select_account"), label: t(".to") }, required: true %>
     <%= f.number_field :amount, label: t(".amount"), required: true, min: 0, placeholder: "100", step: 0.00000001 %>
-    <%= f.date_field :date, value: transfer.date || Date.current, label: t(".date"), required: true, max: Date.current %>
+    <%= f.date_field :date, value: transfer.inflow_transaction&.entry&.date || Date.current, label: t(".date"), required: true, max: Date.current %>
   </section>
 
   <section>
diff --git a/app/views/transfers/_transfer.html.erb b/app/views/transfers/_transfer.html.erb
new file mode 100644
index 00000000..05b8db3b
--- /dev/null
+++ b/app/views/transfers/_transfer.html.erb
@@ -0,0 +1,77 @@
+<%# locals: (transfer:) %>
+
+<%= turbo_frame_tag dom_id(transfer) do %>
+  <div class="grid grid-cols-12 items-center text-gray-900 text-sm font-medium p-4">
+    <div class="pr-10 flex items-center gap-4 col-span-8">
+      <%= check_box_tag dom_id(transfer),
+                        disabled: true,
+                        class: "maybe-checkbox maybe-checkbox--light" %>
+
+      <div class="max-w-full">
+        <%= content_tag :div, class: ["flex items-center gap-2"] do %>
+          <%= render "shared/circle_logo", name: transfer.name, size: "sm" %>
+
+          <div class="truncate">
+            <div class="space-y-0.5">
+
+              <div class="flex items-center gap-2">
+                <%= link_to transfer.name,
+                        transfer_path(transfer),
+                        data: { turbo_frame: "drawer", turbo_prefetch: false },
+                        class: "hover:underline hover:text-gray-800" %>
+
+                <% if transfer.status == "confirmed" %>
+                  <span title="<%= transfer.payment? ? "Payment" : "Transfer" %> is confirmed">
+                    <%= lucide_icon "link-2", class: "w-4 h-4 text-indigo-600" %>
+                  </span>
+                <% elsif transfer.status == "rejected" %>
+                  <span class="inline-flex items-center rounded-full bg-red-50 px-2 py-0.5 text-xs font-medium text-red-700">
+                    Rejected
+                  </span>
+                <% else %>
+                  <span class="inline-flex items-center rounded-full bg-indigo-50 px-2 py-0.5 text-xs font-medium text-indigo-700">
+                    Auto-matched
+                  </span>
+
+                  <%= button_to transfer_path(transfer, transfer: { status: "confirmed" }),
+                    method: :patch,
+                    class: "text-gray-500 hover:text-gray-800 flex items-center justify-center",
+                    title: "Confirm match" do %>
+                    <%= lucide_icon "check", class: "w-4 h-4 text-indigo-400 hover:text-indigo-600" %>
+                  <% end %>
+
+                  <%= button_to transfer_path(transfer, transfer: { status: "rejected" }),
+                    method: :patch,
+                    class: "text-gray-500 hover:text-gray-800 flex items-center justify-center",
+                    title: "Reject match" do %>
+                    <%= lucide_icon "x", class: "w-4 h-4 text-gray-400 hover:text-gray-600" %>
+                  <% end %>
+                <% end %>
+              </div>
+
+              <div class="text-gray-500 text-xs font-normal">
+                <div class="flex items-center gap-1">
+                  <%= link_to transfer.from_account.name, transfer.from_account, class: "hover:underline", data: { turbo_frame: "_top" } %>
+                  <%= lucide_icon "arrow-left-right", class: "w-4 h-4" %>
+                  <%= link_to transfer.to_account.name, transfer.to_account, class: "hover:underline", data: { turbo_frame: "_top" } %>
+                </div>
+              </div>
+            </div>
+          </div>
+        <% end %>
+      </div>
+    </div>
+
+    <div class="flex items-center gap-1 col-span-2">
+      <%= render "categories/badge", category: transfer.payment? ? payment_category : transfer_category %>
+    </div>
+
+    <div class="col-span-2 ml-auto">
+      <p class="flex items-center gap-1">
+        <span>
+          +/- <%= format_money(transfer.amount_abs) %>
+        </span>
+      </p>
+    </div>
+  </div>
+<% end %>
diff --git a/app/views/account/transfers/new.html.erb b/app/views/transfers/new.html.erb
similarity index 100%
rename from app/views/account/transfers/new.html.erb
rename to app/views/transfers/new.html.erb
diff --git a/app/views/account/transfers/show.html.erb b/app/views/transfers/show.html.erb
similarity index 63%
rename from app/views/account/transfers/show.html.erb
rename to app/views/transfers/show.html.erb
index 53e37ecf..f8307997 100644
--- a/app/views/account/transfers/show.html.erb
+++ b/app/views/transfers/show.html.erb
@@ -3,11 +3,11 @@
     <div class="flex items-center gap-4">
       <h3 class="font-medium">
         <span class="text-2xl">
-          <%= format_money @transfer.amount_money %>
+          <%= format_money @transfer.amount_abs %>
         </span>
 
         <span class="text-lg text-gray-500">
-          <%= @transfer.amount_money.currency.iso_code %>
+          <%= @transfer.amount_abs.currency.iso_code %>
         </span>
       </h3>
 
@@ -25,21 +25,21 @@
       <div class="pb-4 px-3 pt-2 text-sm space-y-3 text-gray-900">
         <div class="space-y-3">
           <dl class="flex items-center gap-2 justify-between">
-            <dt class="text-gray-500">To</dt>
+            <dt class="text-gray-500">From</dt>
             <dd class="flex items-center gap-2 font-medium">
-              <%= render "accounts/logo", account: @transfer.inflow_transaction.account, size: "sm" %>
-              <%= @transfer.to_name %>
+              <%= render "accounts/logo", account: @transfer.from_account, size: "sm" %>
+              <%= link_to @transfer.from_account.name, account_path(@transfer.from_account), data: { turbo_frame: "_top" } %>
             </dd>
           </dl>
 
           <dl class="flex items-center gap-2 justify-between">
             <dt class="text-gray-500">Date</dt>
-            <dd class="font-medium"><%= l(@transfer.date, format: :long) %></dd>
+            <dd class="font-medium"><%= l(@transfer.outflow_transaction.entry.date, format: :long) %></dd>
           </dl>
 
           <dl class="flex items-center gap-2 justify-between">
             <dt class="text-gray-500">Amount</dt>
-            <dd class="font-medium text-red-500"><%= format_money -@transfer.amount_money %></dd>
+            <dd class="font-medium text-red-500"><%= format_money -@transfer.amount_abs %></dd>
           </dl>
         </div>
 
@@ -47,21 +47,21 @@
 
         <div class="space-y-3">
           <dl class="flex items-center gap-2 justify-between">
-            <dt class="text-gray-500">From</dt>
+            <dt class="text-gray-500">To</dt>
             <dd class="flex items-center gap-2 font-medium">
-              <%= render "accounts/logo", account: @transfer.outflow_transaction.account, size: "sm" %>
-              <%= @transfer.from_name %>
+              <%= render "accounts/logo", account: @transfer.to_account, size: "sm" %>
+              <%= link_to @transfer.to_account.name, account_path(@transfer.to_account), data: { turbo_frame: "_top" } %>
             </dd>
           </dl>
 
           <dl class="flex items-center gap-2 justify-between">
             <dt class="text-gray-500">Date</dt>
-            <dd class="font-medium"><%= l(@transfer.date, format: :long) %></dd>
+            <dd class="font-medium"><%= l(@transfer.inflow_transaction.entry.date, format: :long) %></dd>
           </dl>
 
           <dl class="flex items-center gap-2 justify-between">
             <dt class="text-gray-500">Amount</dt>
-            <dd class="font-medium text-green-500">+<%= format_money @transfer.amount_money %></dd>
+            <dd class="font-medium text-green-500">+<%= format_money @transfer.amount_abs %></dd>
           </dl>
         </div>
       </div>
@@ -74,7 +74,6 @@
         <%= f.text_area :notes,
                   label: t(".note_label"),
                   placeholder: t(".note_placeholder"),
-                  value: @transfer.outflow_transaction.notes,
                   rows: 5,
                   "data-auto-submit-form-target": "auto" %>
       <% end %>
@@ -83,25 +82,6 @@
     <!-- Settings Section -->
     <%= disclosure t(".settings") do %>
       <div class="pb-4">
-        <%= styled_form_with model: @transfer,
-              class: "p-3", data: { controller: "auto-submit-form" } do |f| %>
-          <div class="flex cursor-pointer items-center gap-2 justify-between">
-            <div class="text-sm space-y-1">
-              <h4 class="text-gray-900"><%= t(".exclude_title") %></h4>
-              <p class="text-gray-500"><%= t(".exclude_subtitle") %></p>
-            </div>
-
-            <div class="relative inline-block select-none">
-              <%= f.check_box :excluded,
-                      checked: @transfer.inflow_transaction.excluded,
-                      class: "sr-only peer",
-                      "data-auto-submit-form-target": "auto" %>
-              <label for="account_transfer_excluded"
-                         class="maybe-switch"></label>
-            </div>
-          </div>
-        <% end %>
-
         <div class="flex items-center justify-between gap-2 p-3">
           <div class="text-sm space-y-1">
             <h4 class="text-gray-900"><%= t(".delete_title") %></h4>
@@ -109,9 +89,9 @@
           </div>
 
           <%= button_to t(".delete"),
-                account_transfer_path(@transfer),
+                transfer_path(@transfer),
                 method: :delete,
-                class:  "rounded-lg px-3 py-2 text-red-500 text-sm
+                class:  "rounded-lg px-3 py-2 whitespace-nowrap text-red-500 text-sm
                           font-medium border border-alpha-black-200",
                 data:   { turbo_confirm: true, turbo_frame: "_top" } %>
         </div>
diff --git a/app/views/transfers/update.turbo_stream.erb b/app/views/transfers/update.turbo_stream.erb
new file mode 100644
index 00000000..90d5a7d5
--- /dev/null
+++ b/app/views/transfers/update.turbo_stream.erb
@@ -0,0 +1,17 @@
+<%= turbo_stream.replace @transfer %>
+
+<%= turbo_stream.replace "category_menu_account_entry_#{@transfer.inflow_transaction.entry.id}",
+  partial: "account/transactions/transaction_category",
+  locals: { entry: @transfer.inflow_transaction.entry } %>
+
+<%= turbo_stream.replace "category_menu_account_entry_#{@transfer.outflow_transaction.entry.id}",
+  partial: "account/transactions/transaction_category",
+  locals: { entry: @transfer.outflow_transaction.entry } %>
+
+<%= turbo_stream.replace "transfer_match_account_entry_#{@transfer.inflow_transaction.entry.id}",
+  partial: "account/transactions/transfer_match",
+  locals: { entry: @transfer.inflow_transaction.entry } %>
+
+<%= turbo_stream.replace "transfer_match_account_entry_#{@transfer.outflow_transaction.entry.id}",
+  partial: "account/transactions/transfer_match",
+  locals: { entry: @transfer.outflow_transaction.entry } %>
diff --git a/config/brakeman.ignore b/config/brakeman.ignore
index ce280c4d..65697755 100644
--- a/config/brakeman.ignore
+++ b/config/brakeman.ignore
@@ -103,6 +103,30 @@
       ],
       "note": ""
     },
+    {
+      "warning_type": "Dangerous Eval",
+      "warning_code": 13,
+      "fingerprint": "c193307bb82f931950d3bf2855f82f9a7f50d94c5bd950ee2803cb8a8abe5253",
+      "check_name": "Evaluation",
+      "message": "Dynamic string evaluated as code",
+      "file": "app/helpers/styled_form_builder.rb",
+      "line": 7,
+      "link": "https://brakemanscanner.org/docs/warning_types/dangerous_eval/",
+      "code": "class_eval(\"      def #{selector}(method, options = {})\\n        merged_options = { class: \\\"form-field__input\\\" }.merge(options)\\n        label = build_label(method, options)\\n        field = super(method, merged_options)\\n\\n        build_styled_field(label, field, merged_options)\\n      end\\n\", \"app/helpers/styled_form_builder.rb\", (7 + 1))",
+      "render_path": null,
+      "location": {
+        "type": "method",
+        "class": "StyledFormBuilder",
+        "method": null
+      },
+      "user_input": null,
+      "confidence": "Weak",
+      "cwe_id": [
+        913,
+        95
+      ],
+      "note": ""
+    },
     {
       "warning_type": "Dynamic Render Path",
       "warning_code": 15,
@@ -138,6 +162,5 @@
       "note": ""
     }
   ],
-  "updated": "2024-12-18 17:46:13 -0500",
-  "brakeman_version": "6.2.2"
+  "brakeman_version": "7.0.0"
 }
diff --git a/config/locales/models/account/transfer/en.yml b/config/locales/models/account/transfer/en.yml
deleted file mode 100644
index c0fe38d5..00000000
--- a/config/locales/models/account/transfer/en.yml
+++ /dev/null
@@ -1,17 +0,0 @@
----
-en:
-  account/transfer:
-    from_fallback_name: Originator
-    name: Transfer from %{from_account} to %{to_account}
-    to_fallback_name: Receiver
-  activerecord:
-    errors:
-      models:
-        account/transfer:
-          attributes:
-            entries:
-              must_be_from_different_accounts: must be from different accounts
-              must_be_marked_as_transfer: must be marked as transfer
-              must_have_an_inflow_and_outflow_that_net_to_zero: must have an inflow
-                and outflow that net to zero
-              must_have_exactly_2_entries: must have exactly 2 entries
diff --git a/config/locales/models/transfer/en.yml b/config/locales/models/transfer/en.yml
new file mode 100644
index 00000000..f373cc8e
--- /dev/null
+++ b/config/locales/models/transfer/en.yml
@@ -0,0 +1,17 @@
+---
+en:
+  activerecord:
+    errors:
+      models:
+        transfer:
+          attributes:
+            base:
+              must_be_from_different_accounts: Transfer must have different accounts
+              must_be_within_date_range: Transfer transaction dates must be within
+                4 days of each other
+              must_have_opposite_amounts: Transfer transactions must have opposite
+                amounts
+              must_have_single_currency: Transfer must have a single currency
+  transfer:
+    name: Transfer to %{to_account}
+    payment_name: Payment to %{to_account}
diff --git a/config/locales/views/account/transactions/en.yml b/config/locales/views/account/transactions/en.yml
index af05bcdf..659c5779 100644
--- a/config/locales/views/account/transactions/en.yml
+++ b/config/locales/views/account/transactions/en.yml
@@ -36,15 +36,8 @@ en:
         no_transactions: No transactions for this account yet.
         transaction: transaction
         transactions: Transactions
-      mark_transfers:
-        success: Marked as transfers
       new:
         new_transaction: New transaction
-      selection_bar:
-        mark_transfers: Mark as transfers?
-        mark_transfers_confirm: Mark as transfers
-        mark_transfers_message: By marking transactions as transfers, they will no
-          longer be included in income or spending calculations.
       show:
         account_label: Account
         amount: Amount
@@ -55,9 +48,6 @@ en:
           balances, and cannot be undone.
         delete_title: Delete transaction
         details: Details
-        exclude_subtitle: This excludes the transaction from any in-app features or
-          analytics.
-        exclude_title: Exclude transaction
         merchant_label: Merchant
         name_label: Name
         nature: Type
@@ -68,5 +58,6 @@ en:
         settings: Settings
         tags_label: Tags
         uncategorized: "(uncategorized)"
-      unmark_transfers:
-        success: Transfer removed
+    transfer_matches:
+      create:
+        success: Transfer created
diff --git a/config/locales/views/account/transfers/en.yml b/config/locales/views/account/transfers/en.yml
deleted file mode 100644
index 7728d764..00000000
--- a/config/locales/views/account/transfers/en.yml
+++ /dev/null
@@ -1,38 +0,0 @@
----
-en:
-  account:
-    transfers:
-      create:
-        success: Transfer created
-      destroy:
-        success: Transfer removed
-      form:
-        amount: Amount
-        date: Date
-        expense: Expense
-        from: From
-        income: Income
-        select_account: Select account
-        submit: Create transfer
-        to: To
-        transfer: Transfer
-      new:
-        title: New transfer
-      show:
-        delete: Delete
-        delete_subtitle: This permanently deletes both of the transactions related
-          to the transfer. This cannot be undone.
-        delete_title: Delete transfer?
-        details: Details
-        exclude_subtitle: This excludes the transfer from any in-app features or analytics.
-        exclude_title: Exclude transfer
-        note_label: Notes
-        note_placeholder: Add a note to this transfer
-        overview: Overview
-        settings: Settings
-      transfer_toggle:
-        remove_transfer: Remove transfer
-        remove_transfer_body: This will remove the transfer from this transaction
-        remove_transfer_confirm: Confirm
-      update:
-        success: Transfer updated
diff --git a/config/locales/views/categories/en.yml b/config/locales/views/categories/en.yml
index 7951e328..1d6aeb6e 100644
--- a/config/locales/views/categories/en.yml
+++ b/config/locales/views/categories/en.yml
@@ -1,11 +1,8 @@
 ---
 en:
-  category:
-    dropdowns:
-      show:
-        empty: No categories found
-        bootstrap: Generate default categories
   categories:
+    bootstrap:
+      success: Default categories created successfully
     category:
       delete: Delete category
       edit: Edit category
@@ -18,15 +15,18 @@ en:
     form:
       placeholder: Category name
     index:
+      bootstrap: Use default categories
       categories: Categories
       empty: No categories found
       new: New category
-      bootstrap: Use default categories
-    bootstrap:
-      success: Default categories created successfully
     menu:
       loading: Loading...
     new:
       new_category: New category
     update:
       success: Category updated successfully
+  category:
+    dropdowns:
+      show:
+        bootstrap: Generate default categories
+        empty: No categories found
diff --git a/config/locales/views/category/dropdowns/en.yml b/config/locales/views/category/dropdowns/en.yml
index 5b9e8248..511e86a9 100644
--- a/config/locales/views/category/dropdowns/en.yml
+++ b/config/locales/views/category/dropdowns/en.yml
@@ -6,7 +6,6 @@ en:
         delete: Delete category
         edit: Edit category
       show:
-        add_new: Add new
-        clear: Clear
+        clear: Clear category
         no_categories: No categories found
         search_placeholder: Search
diff --git a/config/locales/views/transfers/en.yml b/config/locales/views/transfers/en.yml
new file mode 100644
index 00000000..669bae2d
--- /dev/null
+++ b/config/locales/views/transfers/en.yml
@@ -0,0 +1,31 @@
+---
+en:
+  transfers:
+    create:
+      success: Transfer created
+    destroy:
+      success: Transfer removed
+    form:
+      amount: Amount
+      date: Date
+      expense: Expense
+      from: From
+      income: Income
+      select_account: Select account
+      submit: Create transfer
+      to: To
+      transfer: Transfer
+    new:
+      title: New transfer
+    show:
+      delete: Remove transfer
+      delete_subtitle: This removes the transfer.  It will not delete the underlying
+        transactions.
+      delete_title: Remove transfer?
+      details: Details
+      note_label: Notes
+      note_placeholder: Add a note to this transfer
+      overview: Overview
+      settings: Settings
+    update:
+      success: Transfer updated
diff --git a/config/routes.rb b/config/routes.rb
index 73673ced..440756ba 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -46,9 +46,7 @@ Rails.application.routes.draw do
 
   resources :merchants, only: %i[index new create edit update destroy]
 
-  namespace :account do
-    resources :transfers, only: %i[new create destroy show update]
-  end
+  resources :transfers, only: %i[new create destroy show update]
 
   resources :imports, only: %i[index new show create destroy] do
     post :publish, on: :member
@@ -81,6 +79,7 @@ Rails.application.routes.draw do
     resources :entries, only: :index
 
     resources :transactions, only: %i[show new create update destroy] do
+      resource :transfer_match, only: %i[new create]
       resource :category, only: :update, controller: :transaction_categories
 
       collection do
diff --git a/db/migrate/20241231140709_reverse_transfer_relations.rb b/db/migrate/20241231140709_reverse_transfer_relations.rb
new file mode 100644
index 00000000..5dbfe795
--- /dev/null
+++ b/db/migrate/20241231140709_reverse_transfer_relations.rb
@@ -0,0 +1,75 @@
+class ReverseTransferRelations < ActiveRecord::Migration[7.2]
+  def change
+    create_table :transfers, id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
+      t.references :inflow_transaction, null: false, foreign_key: { to_table: :account_transactions }, type: :uuid
+      t.references :outflow_transaction, null: false, foreign_key: { to_table: :account_transactions }, type: :uuid
+      t.string :status, null: false, default: "pending"
+      t.text :notes
+
+      t.index [ :inflow_transaction_id, :outflow_transaction_id ], unique: true
+      t.timestamps
+    end
+
+    reversible do |dir|
+      dir.up do
+        execute <<~SQL
+          INSERT INTO transfers (inflow_transaction_id, outflow_transaction_id, status, created_at, updated_at)
+          SELECT
+            CASE WHEN e1.amount <= 0 THEN e1.entryable_id ELSE e2.entryable_id END as inflow_transaction_id,
+            CASE WHEN e1.amount <= 0 THEN e2.entryable_id ELSE e1.entryable_id END as outflow_transaction_id,
+            'confirmed' as status,
+            e1.created_at,
+            e1.updated_at
+          FROM account_entries e1
+          JOIN account_entries e2 ON
+            e1.transfer_id = e2.transfer_id AND
+            e1.id != e2.id AND
+            e1.id < e2.id -- Ensures we don't duplicate transfers from both sides
+          JOIN accounts a1 ON e1.account_id = a1.id
+          JOIN accounts a2 ON e2.account_id = a2.id
+          WHERE
+            e1.entryable_type = 'Account::Transaction' AND
+            e2.entryable_type = 'Account::Transaction' AND
+            e1.transfer_id IS NOT NULL AND
+            a1.family_id = a2.family_id;
+        SQL
+      end
+
+      dir.down do
+        execute <<~SQL
+          WITH new_transfers AS (
+            INSERT INTO account_transfers (created_at, updated_at)
+            SELECT created_at, updated_at
+            FROM transfers
+            RETURNING id, created_at
+          ),
+          transfer_pairs AS (
+            SELECT
+              nt.id as transfer_id,
+              ae_in.id as inflow_entry_id,
+              ae_out.id as outflow_entry_id
+            FROM transfers t
+            JOIN new_transfers nt ON nt.created_at = t.created_at
+            JOIN account_entries ae_in ON ae_in.entryable_id = t.inflow_transaction_id
+            JOIN account_entries ae_out ON ae_out.entryable_id = t.outflow_transaction_id
+            WHERE
+              ae_in.entryable_type = 'Account::Transaction' AND
+              ae_out.entryable_type = 'Account::Transaction'
+          )
+          UPDATE account_entries ae
+          SET transfer_id = tp.transfer_id
+          FROM transfer_pairs tp
+          WHERE ae.id IN (tp.inflow_entry_id, tp.outflow_entry_id);
+        SQL
+      end
+    end
+
+    remove_foreign_key :account_entries, :account_transfers, column: :transfer_id
+    remove_column :account_entries, :transfer_id, :uuid
+    remove_column :account_entries, :marked_as_transfer, :boolean
+
+    drop_table :account_transfers, id: :uuid, default: -> { "gen_random_uuid()" } do |t|
+      t.timestamps
+    end
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index 0bdce796..7c333cc3 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: 2024_12_27_142333) do
+ActiveRecord::Schema[7.2].define(version: 2024_12_31_140709) do
   # These are extensions that must be enabled in order to support this database
   enable_extension "pgcrypto"
   enable_extension "plpgsql"
@@ -42,8 +42,6 @@ ActiveRecord::Schema[7.2].define(version: 2024_12_27_142333) do
     t.string "name", null: false
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
-    t.uuid "transfer_id"
-    t.boolean "marked_as_transfer", default: false, null: false
     t.uuid "import_id"
     t.text "notes"
     t.boolean "excluded", default: false
@@ -52,7 +50,6 @@ ActiveRecord::Schema[7.2].define(version: 2024_12_27_142333) do
     t.string "enriched_name"
     t.index ["account_id"], name: "index_account_entries_on_account_id"
     t.index ["import_id"], name: "index_account_entries_on_import_id"
-    t.index ["transfer_id"], name: "index_account_entries_on_transfer_id"
   end
 
   create_table "account_holdings", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
@@ -89,11 +86,6 @@ ActiveRecord::Schema[7.2].define(version: 2024_12_27_142333) do
     t.index ["merchant_id"], name: "index_account_transactions_on_merchant_id"
   end
 
-  create_table "account_transfers", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
-    t.datetime "created_at", null: false
-    t.datetime "updated_at", null: false
-  end
-
   create_table "account_valuations", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
@@ -606,6 +598,18 @@ ActiveRecord::Schema[7.2].define(version: 2024_12_27_142333) do
     t.index ["family_id"], name: "index_tags_on_family_id"
   end
 
+  create_table "transfers", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
+    t.uuid "inflow_transaction_id", null: false
+    t.uuid "outflow_transaction_id", null: false
+    t.string "status", default: "pending", null: false
+    t.text "notes"
+    t.datetime "created_at", null: false
+    t.datetime "updated_at", null: false
+    t.index ["inflow_transaction_id", "outflow_transaction_id"], name: "idx_on_inflow_transaction_id_outflow_transaction_id_8cd07a28bd", unique: true
+    t.index ["inflow_transaction_id"], name: "index_transfers_on_inflow_transaction_id"
+    t.index ["outflow_transaction_id"], name: "index_transfers_on_outflow_transaction_id"
+  end
+
   create_table "users", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
     t.uuid "family_id", null: false
     t.string "first_name"
@@ -634,7 +638,6 @@ ActiveRecord::Schema[7.2].define(version: 2024_12_27_142333) do
   end
 
   add_foreign_key "account_balances", "accounts", on_delete: :cascade
-  add_foreign_key "account_entries", "account_transfers", column: "transfer_id"
   add_foreign_key "account_entries", "accounts"
   add_foreign_key "account_entries", "imports"
   add_foreign_key "account_holdings", "accounts"
@@ -663,5 +666,7 @@ ActiveRecord::Schema[7.2].define(version: 2024_12_27_142333) do
   add_foreign_key "sessions", "users"
   add_foreign_key "taggings", "tags"
   add_foreign_key "tags", "families"
+  add_foreign_key "transfers", "account_transactions", column: "inflow_transaction_id"
+  add_foreign_key "transfers", "account_transactions", column: "outflow_transaction_id"
   add_foreign_key "users", "families"
 end
diff --git a/test/controllers/account/trades_controller_test.rb b/test/controllers/account/trades_controller_test.rb
index cdfd6add..66ab86ed 100644
--- a/test/controllers/account/trades_controller_test.rb
+++ b/test/controllers/account/trades_controller_test.rb
@@ -38,7 +38,7 @@ class Account::TradesControllerTest < ActionDispatch::IntegrationTest
 
     assert_difference -> { Account::Entry.count } => 2,
                       -> { Account::Transaction.count } => 2,
-                      -> { Account::Transfer.count } => 1 do
+                      -> { Transfer.count } => 1 do
       post account_trades_url, params: {
         account_entry: {
           account_id: @entry.account_id,
@@ -59,7 +59,7 @@ class Account::TradesControllerTest < ActionDispatch::IntegrationTest
 
     assert_difference -> { Account::Entry.count } => 2,
                       -> { Account::Transaction.count } => 2,
-                      -> { Account::Transfer.count } => 1 do
+                      -> { Transfer.count } => 1 do
       post account_trades_url, params: {
         account_entry: {
           account_id: @entry.account_id,
@@ -78,7 +78,7 @@ class Account::TradesControllerTest < ActionDispatch::IntegrationTest
   test "deposit and withdrawal has optional transfer account" do
     assert_difference -> { Account::Entry.count } => 1,
                       -> { Account::Transaction.count } => 1,
-                      -> { Account::Transfer.count } => 0 do
+                      -> { Transfer.count } => 0 do
       post account_trades_url, params: {
         account_entry: {
           account_id: @entry.account_id,
@@ -93,7 +93,6 @@ class Account::TradesControllerTest < ActionDispatch::IntegrationTest
     created_entry = Account::Entry.order(created_at: :desc).first
 
     assert created_entry.amount.positive?
-    assert created_entry.marked_as_transfer
     assert_redirected_to @entry.account
   end
 
diff --git a/test/controllers/account/transactions_controller_test.rb b/test/controllers/account/transactions_controller_test.rb
index d490bfa7..1b077eb2 100644
--- a/test/controllers/account/transactions_controller_test.rb
+++ b/test/controllers/account/transactions_controller_test.rb
@@ -74,7 +74,7 @@ class Account::TransactionsControllerTest < ActionDispatch::IntegrationTest
   end
 
   test "can destroy many transactions at once" do
-    transactions = @user.family.entries.account_transactions
+    transactions = @user.family.entries.account_transactions.incomes_and_expenses
     delete_count = transactions.size
 
     assert_difference([ "Account::Transaction.count", "Account::Entry.count" ], -delete_count) do
diff --git a/test/controllers/account/transfer_matches_controller_test.rb b/test/controllers/account/transfer_matches_controller_test.rb
new file mode 100644
index 00000000..0e13883e
--- /dev/null
+++ b/test/controllers/account/transfer_matches_controller_test.rb
@@ -0,0 +1,42 @@
+require "test_helper"
+
+class Account::TransferMatchesControllerTest < ActionDispatch::IntegrationTest
+  include Account::EntriesTestHelper
+
+  setup do
+    sign_in @user = users(:family_admin)
+  end
+
+  test "matches existing transaction and creates transfer" do
+    inflow_transaction = create_transaction(amount: 100, account: accounts(:depository))
+    outflow_transaction = create_transaction(amount: -100, account: accounts(:investment))
+
+    assert_difference "Transfer.count", 1 do
+      post account_transaction_transfer_match_path(inflow_transaction), params: {
+        transfer_match: {
+          method: "existing",
+          matched_entry_id: outflow_transaction.id
+        }
+      }
+    end
+
+    assert_redirected_to transactions_url
+    assert_equal "Transfer created", flash[:notice]
+  end
+
+  test "creates transfer for target account" do
+    inflow_transaction = create_transaction(amount: 100, account: accounts(:depository))
+
+    assert_difference [ "Transfer.count", "Account::Entry.count", "Account::Transaction.count" ], 1 do
+      post account_transaction_transfer_match_path(inflow_transaction), params: {
+        transfer_match: {
+          method: "new",
+          target_account_id: accounts(:investment).id
+        }
+      }
+    end
+
+    assert_redirected_to transactions_url
+    assert_equal "Transfer created", flash[:notice]
+  end
+end
diff --git a/test/controllers/account/transfers_controller_test.rb b/test/controllers/transfers_controller_test.rb
similarity index 55%
rename from test/controllers/account/transfers_controller_test.rb
rename to test/controllers/transfers_controller_test.rb
index 72e14345..391937e8 100644
--- a/test/controllers/account/transfers_controller_test.rb
+++ b/test/controllers/transfers_controller_test.rb
@@ -1,19 +1,19 @@
 require "test_helper"
 
-class Account::TransfersControllerTest < ActionDispatch::IntegrationTest
+class TransfersControllerTest < ActionDispatch::IntegrationTest
   setup do
     sign_in users(:family_admin)
   end
 
   test "should get new" do
-    get new_account_transfer_url
+    get new_transfer_url
     assert_response :success
   end
 
   test "can create transfers" do
-    assert_difference "Account::Transfer.count", 1 do
-      post account_transfers_url, params: {
-        account_transfer: {
+    assert_difference "Transfer.count", 1 do
+      post transfers_url, params: {
+        transfer: {
           from_account_id: accounts(:depository).id,
           to_account_id: accounts(:credit_card).id,
           date: Date.current,
@@ -26,8 +26,8 @@ class Account::TransfersControllerTest < ActionDispatch::IntegrationTest
   end
 
   test "can destroy transfer" do
-    assert_difference -> { Account::Transfer.count } => -1, -> { Account::Transaction.count } => -2 do
-      delete account_transfer_url(account_transfers(:one))
+    assert_difference -> { Transfer.count } => -1, -> { Account::Transaction.count } => 0 do
+      delete transfer_url(transfers(:one))
     end
   end
 end
diff --git a/test/fixtures/account/entries.yml b/test/fixtures/account/entries.yml
index 680710be..ccaf29bf 100644
--- a/test/fixtures/account/entries.yml
+++ b/test/fixtures/account/entries.yml
@@ -31,8 +31,6 @@ transfer_out:
   amount: 100
   currency: USD
   account: depository
-  marked_as_transfer: true
-  transfer: one
   entryable_type: Account::Transaction
   entryable: transfer_out
 
@@ -42,7 +40,5 @@ transfer_in:
   amount: -100
   currency: USD
   account: credit_card
-  marked_as_transfer: true
-  transfer: one
   entryable_type: Account::Transaction
   entryable: transfer_in
diff --git a/test/fixtures/account/transfers.yml b/test/fixtures/account/transfers.yml
deleted file mode 100644
index 6aab7788..00000000
--- a/test/fixtures/account/transfers.yml
+++ /dev/null
@@ -1 +0,0 @@
-one: { }
diff --git a/test/fixtures/transfers.yml b/test/fixtures/transfers.yml
new file mode 100644
index 00000000..90c1ea94
--- /dev/null
+++ b/test/fixtures/transfers.yml
@@ -0,0 +1,3 @@
+one:
+  inflow_transaction: transfer_in
+  outflow_transaction: transfer_out
diff --git a/test/models/account/transfer_test.rb b/test/models/account/transfer_test.rb
deleted file mode 100644
index 2c9265c6..00000000
--- a/test/models/account/transfer_test.rb
+++ /dev/null
@@ -1,69 +0,0 @@
-require "test_helper"
-
-class Account::TransferTest < ActiveSupport::TestCase
-  setup do
-    @outflow = account_entries(:transfer_out)
-    @inflow = account_entries(:transfer_in)
-  end
-
-  test "transfer valid if it has inflow and outflow from different accounts for the same amount" do
-    transfer = Account::Transfer.create! entries: [ @inflow, @outflow ]
-
-    assert transfer.valid?
-  end
-
-  test "transfer must have 2 transactions" do
-    invalid_transfer_1 = Account::Transfer.new entries: [ @outflow ]
-    invalid_transfer_2 = Account::Transfer.new entries: [ @inflow, @outflow, account_entries(:transaction) ]
-
-    assert invalid_transfer_1.invalid?
-    assert invalid_transfer_2.invalid?
-  end
-
-  test "transfer cannot have 2 transactions from the same account" do
-    account = accounts(:depository)
-
-    inflow = account.entries.create! \
-      date: Date.current,
-      name: "Inflow",
-      amount: -100,
-      currency: "USD",
-      marked_as_transfer: true,
-      entryable: Account::Transaction.new
-
-    outflow = account.entries.create! \
-      date: Date.current,
-      name: "Outflow",
-      amount: 100,
-      currency: "USD",
-      marked_as_transfer: true,
-      entryable: Account::Transaction.new
-
-    assert_raise ActiveRecord::RecordInvalid do
-      Account::Transfer.create! entries: [ inflow, outflow ]
-    end
-  end
-
-  test "all transfer transactions must be marked as transfers" do
-    @inflow.update! marked_as_transfer: false
-
-    assert_raise ActiveRecord::RecordInvalid do
-      Account::Transfer.create! entries: [ @inflow, @outflow ]
-    end
-  end
-
-  test "single-currency transfer transactions must net to zero" do
-    @outflow.update! amount: 105
-
-    assert_raises ActiveRecord::RecordInvalid do
-      Account::Transfer.create! entries: [ @inflow, @outflow ]
-    end
-  end
-
-  test "multi-currency transfer transactions do not have to net to zero" do
-    @outflow.update! amount: 105, currency: "EUR"
-    transfer = Account::Transfer.create! entries: [ @inflow, @outflow ]
-
-    assert transfer.valid?
-  end
-end
diff --git a/test/models/family_test.rb b/test/models/family_test.rb
index 74376a7e..33088c81 100644
--- a/test/models/family_test.rb
+++ b/test/models/family_test.rb
@@ -120,11 +120,9 @@ class FamilyTest < ActiveSupport::TestCase
 
   test "calculates rolling transaction totals" do
     account = create_account(balance: 1000, accountable: Depository.new)
-    liability_account = create_account(balance: 1000, accountable: Loan.new)
     create_transaction(account: account, date: 2.days.ago.to_date, amount: -500)
     create_transaction(account: account, date: 1.day.ago.to_date, amount: 100)
     create_transaction(account: account, date: Date.current, amount: 20)
-    create_transaction(account: liability_account, date: 2.days.ago.to_date, amount: -333)
 
     snapshot = @family.snapshot_transactions
 
diff --git a/test/models/transfer_test.rb b/test/models/transfer_test.rb
new file mode 100644
index 00000000..a4460fd2
--- /dev/null
+++ b/test/models/transfer_test.rb
@@ -0,0 +1,100 @@
+require "test_helper"
+
+class TransferTest < ActiveSupport::TestCase
+  include Account::EntriesTestHelper
+
+  setup do
+    @outflow = account_transactions(:transfer_out)
+    @inflow = account_transactions(:transfer_in)
+  end
+
+  test "transfer has different accounts, opposing amounts, and within 4 days of each other" do
+    outflow_entry = create_transaction(date: Date.current, account: accounts(:depository), amount: 500)
+    inflow_entry = create_transaction(date: 1.day.ago.to_date, account: accounts(:credit_card), amount: -500)
+
+    assert_difference -> { Transfer.count } => 1 do
+      Transfer.create!(
+        inflow_transaction: inflow_entry.account_transaction,
+        outflow_transaction: outflow_entry.account_transaction,
+      )
+    end
+  end
+
+  test "transfer cannot have 2 transactions from the same account" do
+    outflow_entry = create_transaction(date: Date.current, account: accounts(:depository), amount: 500)
+    inflow_entry = create_transaction(date: 1.day.ago.to_date, account: accounts(:depository), amount: -500)
+
+    transfer = Transfer.new(
+      inflow_transaction: inflow_entry.account_transaction,
+      outflow_transaction: outflow_entry.account_transaction,
+    )
+
+    assert_no_difference -> { Transfer.count } do
+      transfer.save
+    end
+
+    assert_equal "Transfer must have different accounts", transfer.errors.full_messages.first
+  end
+
+  test "Transfer transactions must have opposite amounts" do
+    outflow_entry = create_transaction(date: Date.current, account: accounts(:depository), amount: 500)
+    inflow_entry = create_transaction(date: Date.current, account: accounts(:credit_card), amount: -400)
+
+    transfer = Transfer.new(
+      inflow_transaction: inflow_entry.account_transaction,
+      outflow_transaction: outflow_entry.account_transaction,
+    )
+
+    assert_no_difference -> { Transfer.count } do
+      transfer.save
+    end
+
+    assert_equal "Transfer transactions must have opposite amounts", transfer.errors.full_messages.first
+  end
+
+  test "transfer dates must be within 4 days of each other" do
+    outflow_entry = create_transaction(date: Date.current, account: accounts(:depository), amount: 500)
+    inflow_entry = create_transaction(date: 5.days.ago.to_date, account: accounts(:credit_card), amount: -500)
+
+    transfer = Transfer.new(
+      inflow_transaction: inflow_entry.account_transaction,
+      outflow_transaction: outflow_entry.account_transaction,
+    )
+
+    assert_no_difference -> { Transfer.count } do
+      transfer.save
+    end
+
+    assert_equal "Transfer transaction dates must be within 4 days of each other", transfer.errors.full_messages.first
+  end
+
+  test "from_accounts converts amounts to the to_account's currency" do
+    accounts(:depository).update!(currency: "EUR")
+
+    eur_account = accounts(:depository).reload
+    usd_account = accounts(:credit_card)
+
+    ExchangeRate.create!(
+      from_currency: "EUR",
+      to_currency: "USD",
+      rate: 1.1,
+      date: Date.current,
+    )
+
+    transfer = Transfer.from_accounts(
+      from_account: eur_account,
+      to_account: usd_account,
+      date: Date.current,
+      amount: 500,
+    )
+
+    assert_equal 500, transfer.outflow_transaction.entry.amount
+    assert_equal "EUR", transfer.outflow_transaction.entry.currency
+    assert_equal -550, transfer.inflow_transaction.entry.amount
+    assert_equal "USD", transfer.inflow_transaction.entry.currency
+
+    assert_difference -> { Transfer.count } => 1 do
+      transfer.save!
+    end
+  end
+end
diff --git a/test/system/transactions_test.rb b/test/system/transactions_test.rb
index 26db48c3..76ab1363 100644
--- a/test/system/transactions_test.rb
+++ b/test/system/transactions_test.rb
@@ -210,7 +210,7 @@ class TransactionsTest < ApplicationSystemTestCase
     end
 
     def number_of_transactions_on_page
-      [ @user.family.entries.without_transfers.count, @page_size ].min
+      [ @user.family.entries.count, @page_size ].min
     end
 
     def all_transactions_checkbox
diff --git a/test/system/transfers_test.rb b/test/system/transfers_test.rb
index 601a50f8..a2481b18 100644
--- a/test/system/transfers_test.rb
+++ b/test/system/transfers_test.rb
@@ -19,71 +19,13 @@ class TransfersTest < ApplicationSystemTestCase
 
     select checking_name, from: "From"
     select savings_name, from: "To"
-    fill_in "account_transfer[amount]", with: 500
+    fill_in "transfer[amount]", with: 500
     fill_in "Date", with: transfer_date
 
     click_button "Create transfer"
 
     within "#entry-group-" + transfer_date.to_s do
-      assert_text "Transfer from"
+      assert_text "Payment to"
     end
   end
-
-  test "can match 2 transactions and create a transfer" do
-    transfer_date = Date.current
-    outflow = accounts(:depository).entries.create! \
-      name: "Outflow from checking account",
-      date: transfer_date,
-      amount: 100,
-      currency: "USD",
-      entryable: Account::Transaction.new
-
-    inflow = accounts(:credit_card).entries.create! \
-      name: "Inflow to cc account",
-      date: transfer_date,
-      amount: -100,
-      currency: "USD",
-      entryable: Account::Transaction.new
-
-    visit transactions_url
-
-    transaction_entry_checkbox(inflow).check
-    transaction_entry_checkbox(outflow).check
-
-    bulk_transfer_action_button.click
-
-    click_on "Mark as transfers"
-
-    within "#entry-group-" + transfer_date.to_s do
-      assert_text "Outflow"
-      assert_text "Inflow"
-    end
-  end
-
-  test "can mark a single transaction as a transfer" do
-    txn = @user.family.entries.account_transactions.reverse_chronological.first
-
-    within "#" + dom_id(txn) do
-      assert_text txn.account_transaction.category.name || "Uncategorized"
-    end
-
-    transaction_entry_checkbox(txn).check
-
-    bulk_transfer_action_button.click
-    click_on "Mark as transfers"
-
-    within "#" + dom_id(txn) do
-      assert_no_text "Uncategorized"
-    end
-  end
-
-  private
-
-    def transaction_entry_checkbox(transaction_entry)
-      find("#" + dom_id(transaction_entry, "selection"))
-    end
-
-    def bulk_transfer_action_button
-      find("#bulk-transfer-btn")
-    end
 end