diff --git a/app/controllers/application_controller.rb b/app/controllers/application_controller.rb
index 4ab192b4..44a94d12 100644
--- a/app/controllers/application_controller.rb
+++ b/app/controllers/application_controller.rb
@@ -2,26 +2,10 @@ class ApplicationController < ActionController::Base
   include Onboardable, Localize, AutoSync, Authentication, Invitable, SelfHostable, StoreLocation, Impersonatable, Breadcrumbable, FeatureGuardable, Notifiable
   include Pagy::Backend
 
-  helper_method :require_upgrade?, :subscription_pending?
-
   before_action :detect_os
   before_action :set_default_chat
 
   private
-    def require_upgrade?
-      return false if self_hosted?
-      return false unless Current.session
-      return false if Current.family.subscribed?
-      return false if subscription_pending? || request.path == settings_billing_path
-
-      true
-    end
-
-    def subscription_pending?
-      subscribed_at = Current.session.subscribed_at
-      subscribed_at.present? && subscribed_at <= Time.current && subscribed_at > 1.hour.ago
-    end
-
     def detect_os
       user_agent = request.user_agent
       @os = case user_agent
diff --git a/app/controllers/concerns/onboardable.rb b/app/controllers/concerns/onboardable.rb
index d39c228d..804667b4 100644
--- a/app/controllers/concerns/onboardable.rb
+++ b/app/controllers/concerns/onboardable.rb
@@ -3,16 +3,24 @@ module Onboardable
 
   included do
     before_action :require_onboarding_and_upgrade
+    helper_method :subscription_pending?
   end
 
   private
+    # A subscription goes into "pending" mode immediately after checkout, but before webhooks are processed.
+    def subscription_pending?
+      subscribed_at = Current.session.subscribed_at
+      subscribed_at.present? && subscribed_at <= Time.current && subscribed_at > 1.hour.ago
+    end
+
+    # First, we require onboarding, then once that's complete, we require an upgrade for non-subscribed users.
     def require_onboarding_and_upgrade
       return unless Current.user
       return unless redirectable_path?(request.path)
 
       if Current.user.onboarded_at.blank?
         redirect_to onboarding_path
-      elsif !Current.family.subscribed?
+      elsif !Current.family.subscribed? && !Current.family.trialing?
         redirect_to upgrade_subscription_path
       end
     end
diff --git a/app/controllers/subscriptions_controller.rb b/app/controllers/subscriptions_controller.rb
index 4c110dd6..895c7192 100644
--- a/app/controllers/subscriptions_controller.rb
+++ b/app/controllers/subscriptions_controller.rb
@@ -38,7 +38,7 @@ class SubscriptionsController < ApplicationController
     end
 
     checkout_session_url = stripe.get_checkout_session_url(
-      price_id,
+      price_id: price_id,
       customer_id: Current.family.stripe_customer_id,
       success_url: success_subscription_url + "?session_id={CHECKOUT_SESSION_ID}",
       cancel_url: upgrade_subscription_url(plan: params[:plan])
@@ -49,7 +49,7 @@ class SubscriptionsController < ApplicationController
 
   def show
     portal_session_url = stripe.get_billing_portal_session_url(
-      Current.family.stripe_customer_id,
+      customer_id: Current.family.stripe_customer_id,
       return_url: settings_billing_url
     )
 
diff --git a/app/models/demo/generator.rb b/app/models/demo/generator.rb
index 5b096b87..a7ce8940 100644
--- a/app/models/demo/generator.rb
+++ b/app/models/demo/generator.rb
@@ -2,7 +2,7 @@ class Demo::Generator
   COLORS = %w[#e99537 #4da568 #6471eb #db5a54 #df4e92 #c44fe9 #eb5429 #61c9ea #805dee #6ad28a]
 
   # Builds a semi-realistic mirror of what production data might look like
-  def reset_and_clear_data!(family_names)
+  def reset_and_clear_data!(family_names, require_onboarding: false)
     puts "Clearing existing data..."
 
     destroy_everything!
@@ -10,7 +10,7 @@ class Demo::Generator
     puts "Data cleared"
 
     family_names.each_with_index do |family_name, index|
-      create_family_and_user!(family_name, "user#{index == 0 ? "" : index + 1}@maybe.local")
+      create_family_and_user!(family_name, "user#{index == 0 ? "" : index + 1}@maybe.local", require_onboarding: require_onboarding)
     end
 
     puts "Users reset"
@@ -152,7 +152,7 @@ class Demo::Generator
       Security::Price.destroy_all
     end
 
-    def create_family_and_user!(family_name, user_email, currency: "USD", subscription_status: "active")
+    def create_family_and_user!(family_name, user_email, currency: "USD", require_onboarding: false)
       base_uuid = "d99e3c6e-d513-4452-8f24-dc263f8528c0"
       id = Digest::UUID.uuid_v5(base_uuid, family_name)
 
@@ -160,7 +160,7 @@ class Demo::Generator
         id: id,
         name: family_name,
         currency: currency,
-        stripe_subscription_status: subscription_status,
+        stripe_subscription_status: require_onboarding ? nil : "active",
         locale: "en",
         country: "US",
         timezone: "America/New_York",
@@ -173,7 +173,7 @@ class Demo::Generator
         last_name: "User",
         role: "admin",
         password: "password",
-        onboarded_at: Time.current
+        onboarded_at: require_onboarding ? nil : Time.current
 
       family.users.create! \
         email: "member_#{user_email}",
@@ -181,7 +181,7 @@ class Demo::Generator
         last_name: "User",
         role: "member",
         password: "password",
-        onboarded_at: Time.current
+        onboarded_at: require_onboarding ? nil : Time.current
     end
 
     def create_rules!(family)
diff --git a/app/models/family.rb b/app/models/family.rb
index 923a7566..0adb1521 100644
--- a/app/models/family.rb
+++ b/app/models/family.rb
@@ -128,11 +128,15 @@ class Family < ApplicationRecord
   end
 
   def subscribed?
-    trialing? || stripe_subscription_status == "active"
+    stripe_subscription_status == "active"
   end
 
   def trialing?
-    trial_started_at.present? && trial_started_at <= 14.days.from_now
+    !subscribed? && trial_started_at.present? && trial_started_at <= 14.days.from_now
+  end
+
+  def trial_remaining_days
+    (14 - (Time.current - trial_started_at).to_i / 86400).to_i
   end
 
   def existing_customer?
diff --git a/app/models/provider/stripe.rb b/app/models/provider/stripe.rb
index 37d59e0a..09c67911 100644
--- a/app/models/provider/stripe.rb
+++ b/app/models/provider/stripe.rb
@@ -30,14 +30,14 @@ class Provider::Stripe
     end
   end
 
-  def create_customer(email, metadata: {})
+  def create_customer(email:, metadata: {})
     client.v1.customers.create(
       email: email,
       metadata: metadata
     )
   end
 
-  def get_checkout_session_url(price_id, customer_id: nil, success_url: nil, cancel_url: nil)
+  def get_checkout_session_url(price_id:, customer_id: nil, success_url: nil, cancel_url: nil)
     client.v1.checkout.sessions.create(
       customer: customer_id,
       line_items: [ { price: price_id, quantity: 1 } ],
@@ -48,7 +48,7 @@ class Provider::Stripe
     ).url
   end
 
-  def get_billing_portal_session_url(customer_id, return_url: nil)
+  def get_billing_portal_session_url(customer_id:, return_url: nil)
     client.v1.billing_portal.sessions.create(
       customer: customer_id,
       return_url: return_url
diff --git a/app/views/onboardings/show.html.erb b/app/views/onboardings/show.html.erb
index 4f58ac51..9a2837e6 100644
--- a/app/views/onboardings/show.html.erb
+++ b/app/views/onboardings/show.html.erb
@@ -24,23 +24,25 @@
       </div>
 
       <div class="flex flex-col md:flex-row md:justify-between md:items-center md:gap-4 space-y-4 md:space-y-0 mb-4">
-        <%= form.text_field :first_name, placeholder: t(".first_name"), label: t(".first_name"), container_class: "bg-container md:w-1/2 w-full", required: true %>
-        <%= form.text_field :last_name, placeholder: t(".last_name"), label: t(".last_name"), container_class: "bg-container md:w-1/2 w-full", required: true %>
+        <%= form.text_field :first_name, placeholder: "First name", label: "First name", container_class: "bg-container md:w-1/2 w-full", required: true %>
+        <%= form.text_field :last_name, placeholder: "Last name", label: "Last name", container_class: "bg-container md:w-1/2 w-full", required: true %>
       </div>
 
       <% unless @invitation %>
         <div class="space-y-4 mb-4">
           <%= form.fields_for :family do |family_form| %>
-            <%= family_form.text_field :name, placeholder: t(".household_name"), label: t(".household_name") %>
+            <%= family_form.text_field :name, placeholder: "Household name", label: "Household name" %>
 
             <%= family_form.select :country,
               country_options,
-              { label: t(".country") }, required: true %>
+              { label: "Country" },
+              required: true
+            %>
           <% end %>
         </div>
       <% end %>
 
-      <%= form.submit t(".submit") %>
+      <%= form.submit "Continue" %>
     <% end %>
   </div>
 </div>
diff --git a/app/views/settings/billings/show.html.erb b/app/views/settings/billings/show.html.erb
index 6775d46a..221cdaad 100644
--- a/app/views/settings/billings/show.html.erb
+++ b/app/views/settings/billings/show.html.erb
@@ -4,12 +4,25 @@
   <div class="space-y-4">
     <div class="p-3 shadow-border-xs bg-container rounded-lg flex justify-between items-center">
       <div class="flex items-center gap-3">
-        <div class="w-9 h-9 rounded-full bg-gray-25 flex justify-center items-center">
-          <%= icon "gem" %>
-        </div>
+        <%= render FilledIconComponent.new(
+          icon: "gem",
+          rounded: true,
+          size: "lg"
+        ) %>
 
         <div class="text-sm space-y-1">
-          <% if @user.family.subscribed? || subscription_pending? %>
+          <% if subscription_pending? %>
+            <p class="text-primary">
+              Your subscription is pending. You can still use Maybe+ while we process your subscription.
+            </p>
+          <% elsif @user.family.trialing? %>
+            <p class="text-primary">
+              You are currently trialing <span class="font-medium">Maybe+</span>
+              <span class="text-secondary">
+                (<%= @user.family.trial_remaining_days %> days remaining)
+              </span>
+            </p>
+          <% elsif @user.family.subscribed? %>
             <p class="text-primary">You are currently subscribed to <span class="font-medium">Maybe+</span></p>
           <% else %>
             <p class="text-primary">You are currently <span class="font-medium">not subscribed</span></p>
@@ -18,7 +31,7 @@
         </div>
       </div>
 
-      <% if @user.family.subscribed? || subscription_pending? %>
+      <% if @user.family.subscribed? %>
         <%= render LinkComponent.new(
           text: "Manage",
           icon: "external-link",
@@ -27,13 +40,13 @@
           href: subscription_path,
           rel: "noopener"
         ) %>
-      <% else %>
+      <% elsif @user.family.trialing? && !subscription_pending? %>
         <%= render LinkComponent.new(
-          text: "Subscribe",
+          text: "Choose plan",
           variant: "primary",
-          icon: "external-link",
+          icon: "plus",
           icon_position: "right",
-          href: new_subscription_path,
+          href: upgrade_subscription_path(view: "upgrade"),
           rel: "noopener") %>
       <% end %>
     </div>
diff --git a/app/views/subscriptions/upgrade.html.erb b/app/views/subscriptions/upgrade.html.erb
index d005fd5a..b66e927b 100644
--- a/app/views/subscriptions/upgrade.html.erb
+++ b/app/views/subscriptions/upgrade.html.erb
@@ -17,7 +17,11 @@
   <div class="grow flex flex-col items-center justify-center">
     <%= image_tag "logo-color.png", class: "w-16 mb-6" %>
 
-    <p class="text-xl lg:text-3xl text-primary font-display font-medium">Your trial is over</p>
+    <% if Current.family.trialing? %>
+      <p class="text-xl lg:text-3xl text-primary font-display font-medium">Your trial has <%= Current.family.trial_remaining_days %> days remaining</p>
+    <% else %>
+      <p class="text-xl lg:text-3xl text-primary font-display font-medium">Your trial is over</p>
+    <% end %>
 
     <h2 class="text-xl lg:text-3xl font-display font-medium mb-2">
       <span class="text-secondary">Unlock</span>
diff --git a/config/environments/development.rb b/config/environments/development.rb
index 261671b2..553da47e 100644
--- a/config/environments/development.rb
+++ b/config/environments/development.rb
@@ -35,7 +35,9 @@ Rails.application.configure do
 
   # Store uploaded files on the local file system (see config/storage.yml for options).
   config.active_storage.service = ENV.fetch("ACTIVE_STORAGE_SERVICE", "local").to_sym
-  config.active_storage.default_url_options = { host: "localhost", port: 3000 }
+  config.after_initialize do
+    ActiveStorage::Current.url_options = { host: "localhost", port: 3000 }
+  end
 
   # Set Active Storage URL expiration time to 7 days
   config.active_storage.urls_expire_in = 7.days
diff --git a/lib/tasks/demo_data.rake b/lib/tasks/demo_data.rake
index 2f5a1b6d..c57a006f 100644
--- a/lib/tasks/demo_data.rake
+++ b/lib/tasks/demo_data.rake
@@ -5,6 +5,11 @@ namespace :demo_data do
     Demo::Generator.new.reset_and_clear_data!(families)
   end
 
+  task new_user: :environment do
+    families = [ "Demo Family 1" ]
+    Demo::Generator.new.reset_and_clear_data!(families, require_onboarding: true)
+  end
+
   task :reset, [ :count ] => :environment do |t, args|
     count = (args[:count] || 1).to_i
     families = count.times.map { |i| "Demo Family #{i + 1}" }