diff --git a/lib/ruby_llm/active_record/acts_as_legacy.rb b/lib/ruby_llm/active_record/acts_as_legacy.rb
index dc576f878..ae91e7047 100644
--- a/lib/ruby_llm/active_record/acts_as_legacy.rb
+++ b/lib/ruby_llm/active_record/acts_as_legacy.rb
@@ -456,6 +456,7 @@ def prepare_content_for_storage(content)
     # Methods mixed into message models.
     module MessageLegacyMethods
       extend ActiveSupport::Concern
+      include ContentExtraction
 
       class_methods do
         attr_reader :chat_class, :tool_call_class, :chat_foreign_key, :tool_call_foreign_key
@@ -494,20 +495,23 @@ def extract_tool_call_id
       end
 
       def extract_content
-        text_content = if content.respond_to?(:to_plain_text)
-                         content.to_plain_text
-                       else
-                         content
-                       end
+        content_value = content
+        text_content = plain_text_content(content_value)
+        action_text_attachments = action_text_attachment_sources(content_value)
 
-        return text_content unless respond_to?(:attachments) && attachments.attached?
+        has_active_storage_attachments = respond_to?(:attachments) && attachments.attached?
+        return text_content if action_text_attachments.empty? && !has_active_storage_attachments
 
         RubyLLM::Content.new(text_content).tap do |content_obj|
           @_tempfiles = []
 
-          attachments.each do |attachment|
-            tempfile = download_attachment(attachment)
-            content_obj.add_attachment(tempfile, filename: attachment.filename.to_s)
+          add_action_text_attachments(content_obj, action_text_attachments)
+
+          if has_active_storage_attachments
+            attachments.each do |attachment|
+              tempfile = download_attachment(attachment)
+              content_obj.add_attachment(tempfile, filename: attachment.filename.to_s)
+            end
           end
         end
       end
diff --git a/lib/ruby_llm/active_record/content_extraction.rb b/lib/ruby_llm/active_record/content_extraction.rb
new file mode 100644
index 000000000..380864e77
--- /dev/null
+++ b/lib/ruby_llm/active_record/content_extraction.rb
@@ -0,0 +1,65 @@
+# frozen_string_literal: true
+
+module RubyLLM
+  module ActiveRecord
+    # Shared helpers for converting persisted Active Record message content into RubyLLM content.
+    module ContentExtraction
+      private
+
+      def plain_text_content(content_value)
+        return content_value.to_plain_text if content_value.respond_to?(:to_plain_text)
+
+        content_value
+      end
+
+      def action_text_attachment_sources(content_value)
+        return [] unless content_value.respond_to?(:body)
+
+        body = content_value.body
+        return [] unless body.respond_to?(:attachables)
+
+        body.attachables.filter_map { |attachable| active_storage_source_for(attachable) }.flatten
+      end
+
+      def active_storage_source_for(attachable)
+        return unless defined?(::ActiveStorage)
+
+        return attachable if active_storage_blob?(attachable)
+        return attachable.blob if active_storage_attachment?(attachable)
+        return attachable.blob if active_storage_attached_one?(attachable)
+        return attachable.blobs if active_storage_attached_many?(attachable)
+
+        attachable.blob if attachable.respond_to?(:blob)
+      end
+
+      def active_storage_blob?(source)
+        defined?(::ActiveStorage::Blob) && source.is_a?(::ActiveStorage::Blob)
+      end
+
+      def active_storage_attachment?(source)
+        defined?(::ActiveStorage::Attachment) && source.is_a?(::ActiveStorage::Attachment)
+      end
+
+      def active_storage_attached_one?(source)
+        defined?(::ActiveStorage::Attached::One) && source.is_a?(::ActiveStorage::Attached::One)
+      end
+
+      def active_storage_attached_many?(source)
+        defined?(::ActiveStorage::Attached::Many) && source.is_a?(::ActiveStorage::Attached::Many)
+      end
+
+      def add_action_text_attachments(content_obj, sources)
+        sources.each do |source|
+          content_obj.add_attachment(source, filename: active_storage_filename(source))
+        end
+      end
+
+      def active_storage_filename(source)
+        return source.filename.to_s if active_storage_blob?(source)
+        return source.blob.filename.to_s if active_storage_attachment?(source)
+
+        source.blob.filename.to_s if active_storage_attached_one?(source) && source.blob
+      end
+    end
+  end
+end
diff --git a/lib/ruby_llm/active_record/message_methods.rb b/lib/ruby_llm/active_record/message_methods.rb
index f6ca9a114..729e9d043 100644
--- a/lib/ruby_llm/active_record/message_methods.rb
+++ b/lib/ruby_llm/active_record/message_methods.rb
@@ -9,6 +9,7 @@ module ActiveRecord
     module MessageMethods
       extend ActiveSupport::Concern
       include PayloadHelpers
+      include ContentExtraction
 
       class_methods do
         attr_reader :chat_class, :tool_call_class, :chat_foreign_key, :tool_call_foreign_key
@@ -115,16 +116,22 @@ def extract_content
         return RubyLLM::Content::Raw.new(content_raw) if has_attribute?(:content_raw) && content_raw.present?
 
         content_value = content
-        content_value = content_value.to_plain_text if content_value.respond_to?(:to_plain_text)
+        content_text = plain_text_content(content_value)
+        action_text_attachments = action_text_attachment_sources(content_value)
 
-        return content_value unless respond_to?(:attachments) && attachments.attached?
+        has_active_storage_attachments = respond_to?(:attachments) && attachments.attached?
+        return content_text if action_text_attachments.empty? && !has_active_storage_attachments
 
-        RubyLLM::Content.new(content_value).tap do |content_obj|
+        RubyLLM::Content.new(content_text).tap do |content_obj|
           @_tempfiles = []
 
-          attachments.each do |attachment|
-            tempfile = download_attachment(attachment)
-            content_obj.add_attachment(tempfile, filename: attachment.filename.to_s)
+          add_action_text_attachments(content_obj, action_text_attachments)
+
+          if has_active_storage_attachments
+            attachments.each do |attachment|
+              tempfile = download_attachment(attachment)
+              content_obj.add_attachment(tempfile, filename: attachment.filename.to_s)
+            end
           end
         end
       end
diff --git a/spec/dummy/db/migrate/20260506120000_create_action_text_tables.action_text.rb b/spec/dummy/db/migrate/20260506120000_create_action_text_tables.action_text.rb
new file mode 100644
index 000000000..255266dfe
--- /dev/null
+++ b/spec/dummy/db/migrate/20260506120000_create_action_text_tables.action_text.rb
@@ -0,0 +1,16 @@
+# frozen_string_literal: true
+
+# This migration comes from action_text (originally 20180528164100)
+class CreateActionTextTables < ActiveRecord::Migration[7.0]
+  def change
+    create_table :action_text_rich_texts do |t|
+      t.string :name, null: false
+      t.text :body
+      t.references :record, null: false, polymorphic: true, index: false
+
+      t.timestamps
+
+      t.index %i[record_type record_id name], name: :index_action_text_rich_texts_uniqueness, unique: true
+    end
+  end
+end
diff --git a/spec/dummy/db/schema.rb b/spec/dummy/db/schema.rb
index 52e1bb7f6..01a54fc68 100644
--- a/spec/dummy/db/schema.rb
+++ b/spec/dummy/db/schema.rb
@@ -12,7 +12,17 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema[7.1].define(version: 20_251_021_170_000) do
+ActiveRecord::Schema[7.1].define(version: 20_260_506_120_000) do
+  create_table 'action_text_rich_texts', force: :cascade do |t|
+    t.string 'name', null: false
+    t.text 'body'
+    t.string 'record_type', null: false
+    t.bigint 'record_id', null: false
+    t.datetime 'created_at', null: false
+    t.datetime 'updated_at', null: false
+    t.index %w[record_type record_id name], name: 'index_action_text_rich_texts_uniqueness', unique: true
+  end
+
   create_table 'active_storage_attachments', force: :cascade do |t|
     t.string 'name', null: false
     t.string 'record_type', null: false
diff --git a/spec/ruby_llm/active_record/acts_as_action_text_spec.rb b/spec/ruby_llm/active_record/acts_as_action_text_spec.rb
index 582267bd1..44e01922f 100644
--- a/spec/ruby_llm/active_record/acts_as_action_text_spec.rb
+++ b/spec/ruby_llm/active_record/acts_as_action_text_spec.rb
@@ -1,60 +1,147 @@
 # frozen_string_literal: true
 
 require 'rails_helper'
+require 'stringio'
 
 RSpec.describe RubyLLM::ActiveRecord::ActsAs do
   include_context 'with configured RubyLLM'
 
-  let(:chat) { Chat.create! }
+  before(:all) do # rubocop:disable RSpec/BeforeAfterAll
+    ActiveRecord::Migration.suppress_messages do
+      ActiveRecord::Migration.create_table :action_text_chats, force: true do |t|
+        t.references :model
+        t.timestamps
+      end
+
+      ActiveRecord::Migration.create_table :action_text_messages, force: true do |t|
+        t.references :action_text_chat
+        t.string :role
+        t.text :content
+        t.json :content_raw
+        t.references :model
+        t.integer :input_tokens
+        t.integer :output_tokens
+        t.integer :cached_tokens
+        t.integer :cache_creation_tokens
+        t.text :thinking_signature
+        t.text :thinking_text
+        t.integer :thinking_tokens
+        t.references :action_text_tool_call
+        t.timestamps
+      end
+
+      ActiveRecord::Migration.create_table :action_text_tool_calls, force: true do |t|
+        t.references :action_text_message
+        t.string :tool_call_id
+        t.string :name
+        t.text :thought_signature
+        t.json :arguments
+        t.timestamps
+      end
+    end
+  end
 
-  def mock_action_text(plain_text)
-    instance_double(ActionText::RichText).tap do |mock|
-      allow(mock).to receive(:to_plain_text).and_return(plain_text)
+  after(:all) do # rubocop:disable RSpec/BeforeAfterAll
+    ActiveRecord::Migration.suppress_messages do
+      if ActiveRecord::Base.connection.table_exists?(:action_text_tool_calls)
+        ActiveRecord::Migration.drop_table :action_text_tool_calls
+      end
+      if ActiveRecord::Base.connection.table_exists?(:action_text_messages)
+        ActiveRecord::Migration.drop_table :action_text_messages
+      end
+      if ActiveRecord::Base.connection.table_exists?(:action_text_chats)
+        ActiveRecord::Migration.drop_table :action_text_chats
+      end
     end
   end
 
-  def create_message_with_action_text(content_text)
-    message = chat.messages.create!(role: :user)
-    action_text_content = mock_action_text(content_text)
-    allow(message).to receive(:content).and_return(action_text_content)
-    [message, action_text_content]
+  class ActionTextChat < ActiveRecord::Base # rubocop:disable Lint/ConstantDefinitionInBlock,RSpec/LeakyConstantDeclaration
+    acts_as_chat messages: :action_text_messages, message_class: 'ActionTextMessage'
+  end
+
+  class ActionTextMessage < ActiveRecord::Base # rubocop:disable Lint/ConstantDefinitionInBlock,RSpec/LeakyConstantDeclaration
+    acts_as_message chat: :action_text_chat,
+                    chat_class: 'ActionTextChat',
+                    tool_calls: :action_text_tool_calls,
+                    tool_call_class: 'ActionTextToolCall'
+    has_rich_text :content
+    has_many_attached :attachments
+  end
+
+  class ActionTextToolCall < ActiveRecord::Base # rubocop:disable Lint/ConstantDefinitionInBlock,RSpec/LeakyConstantDeclaration
+    acts_as_tool_call message: :action_text_message, message_class: 'ActionTextMessage'
+  end
+
+  let(:chat) { ActionTextChat.create! }
+
+  def create_blob(content: 'test data', filename: 'test.txt', content_type: 'text/plain')
+    ActiveStorage::Blob.create_and_upload!(
+      io: StringIO.new(content),
+      filename: filename,
+      content_type: content_type
+    )
   end
 
   describe 'Action Text content extraction' do
-    context 'when content responds to to_plain_text' do
+    context 'when the message model has rich text content' do
       it 'extracts plain text from Action Text content' do
-        message, action_text_content = create_message_with_action_text('This is plain text')
+        message = chat.action_text_messages.create!(
+          role: :user,
+          content: '<div>This is <strong>plain</strong> text</div>'
+        )
 
         llm_message = message.to_llm
 
-        expect(action_text_content).to have_received(:to_plain_text)
+        expect(message.content).to be_a(ActionText::RichText)
+        expect(message[:content]).to be_nil
         expect(llm_message.content).to eq('This is plain text')
       end
     end
 
-    context 'when content is a regular string' do
+    context 'when the message model uses a regular text column' do
       it 'returns content unchanged' do
-        message = chat.messages.create!(role: :user, content: 'Regular text content')
+        message = Chat.create!.messages.create!(role: :user, content: 'Regular text content')
 
+        expect(message.content).to eq('Regular text content')
         expect(message.to_llm.content).to eq('Regular text content')
       end
     end
 
-    context 'when Action Text content has attachments' do
-      let(:test_attachment) do
-        { io: StringIO.new('test data'), filename: 'test.txt', content_type: 'text/plain' }
+    context 'when the rich text message has Active Storage attachments' do
+      it 'combines Action Text content with model attachments into RubyLLM::Content' do
+        message = chat.action_text_messages.create!(
+          role: :user,
+          content: '<div>Rich text with attachment</div>'
+        )
+        message.attachments.attach(
+          io: StringIO.new('test data'),
+          filename: 'test.txt',
+          content_type: 'text/plain'
+        )
+
+        llm_message = message.to_llm
+
+        expect(llm_message.content).to be_a(RubyLLM::Content)
+        expect(llm_message.content.text).to eq('Rich text with attachment')
+        expect(llm_message.content.attachments.first.mime_type).to eq('text/plain')
       end
 
-      it 'combines Action Text with attachments into RubyLLM::Content' do
-        message, action_text_content = create_message_with_action_text('Rich text with attachment')
-        message.attachments.attach(test_attachment)
+      it 'extracts embedded Action Text attachments into RubyLLM::Content' do
+        blob = create_blob(content: 'embedded file data', filename: 'embedded.txt')
+        attachment = ActionText::Attachment.from_attachable(blob)
+        message = chat.action_text_messages.create!(
+          role: :user,
+          content: "<div>See file:</div>#{attachment.to_html}"
+        )
 
         llm_message = message.to_llm
 
-        expect(action_text_content).to have_received(:to_plain_text)
+        expect(message.content.body.attachables).to include(blob)
         expect(llm_message.content).to be_a(RubyLLM::Content)
-        expect(llm_message.content.text).to eq('Rich text with attachment')
+        expect(llm_message.content.text).to include('See file:')
+        expect(llm_message.content.attachments.first.filename).to eq('embedded.txt')
         expect(llm_message.content.attachments.first.mime_type).to eq('text/plain')
+        expect(llm_message.content.attachments.first.content).to eq('embedded file data')
       end
     end
   end