chore: fixes

app/jobs/conversation_reply_email_job.rb

@@ -0,0 +1,15 @@
+class ConversationReplyEmailJob < ApplicationJob
+  queue_as :mailers
+
+  def perform(conversation_id, last_queued_id)
+    conversation = Conversation.find(conversation_id)
+
+    if conversation.messages.incoming&.last&.content_type == 'incoming_email'
+      ConversationReplyMailer.with(account: conversation.account).reply_without_summary(conversation, last_queued_id).deliver_later
+    else
+      ConversationReplyMailer.with(account: conversation.account).reply_with_summary(conversation, last_queued_id).deliver_later
+    end
+
+    Redis::Alfred.delete(format(::Redis::Alfred::CONVERSATION_MAILER_KEY, conversation_id: conversation.id))
+  end
+end

app/services/messages/send_email_notification_service.rb

@@ -12,7 +12,7 @@ class Messages::SendEmailNotificationService
     # the worker never manages to clean up.
     return unless Redis::Alfred.set(conversation_mail_key, message.id, nx: true, ex: 1.hour.to_i)
 
-    ConversationReplyEmailWorker.perform_in(2.minutes, conversation.id, message.id)
+    ConversationReplyEmailJob.set(wait: 2.minutes).perform_later(conversation.id, message.id)
   end
 
   private

app/workers/conversation_reply_email_worker.rb

@@ -1,29 +0,0 @@
-# TODO: lets move this to active job, since thats what we use over all
-class ConversationReplyEmailWorker
-  include Sidekiq::Worker
-  sidekiq_options queue: :mailers
-
-  def perform(conversation_id, last_queued_id)
-    @conversation = Conversation.find(conversation_id)
-
-    # send the email
-    if @conversation.messages.incoming&.last&.content_type == 'incoming_email'
-      ConversationReplyMailer.with(account: @conversation.account).reply_without_summary(@conversation, last_queued_id).deliver_later
-    else
-      ConversationReplyMailer.with(account: @conversation.account).reply_with_summary(@conversation, last_queued_id).deliver_later
-    end
-
-    # delete the redis set from the first new message on the conversation
-    Redis::Alfred.delete(conversation_mail_key)
-  end
-
-  private
-
-  def email_inbox?
-    @conversation.inbox&.inbox_type == 'Email'
-  end
-
-  def conversation_mail_key
-    format(::Redis::Alfred::CONVERSATION_MAILER_KEY, conversation_id: @conversation.id)
-  end
-end

config/initializers/sidekiq.rb

@@ -9,7 +9,8 @@ end
 # Logs whenever a job is pulled off Redis for execution.
 class ChatwootDequeuedLogger
   def call(_worker, job, queue)
-    Sidekiq.logger.info("Dequeued #{job['class']} #{job['jid']} from #{queue}")
+    payload = job['args'].first
+    Sidekiq.logger.info("Dequeued #{job['wrapped']} #{payload['job_id']} from #{queue}")
     yield
   end
 end

enterprise/app/models/captain/document.rb

@@ -47,7 +47,7 @@ class Captain::Document < ApplicationRecord
   after_create_commit :enqueue_crawl_job
   after_create_commit :update_document_usage
   after_destroy :update_document_usage
-  after_commit :enqueue_response_builder_job, on: :update, if: :should_enqueue_response_builder?
+  after_commit :enqueue_response_builder_job
   scope :ordered, -> { order(created_at: :desc) }
 
   scope :for_account, ->(account_id) { where(account_id: account_id) }
@@ -94,15 +94,18 @@ class Captain::Document < ApplicationRecord
   end
 
   def enqueue_response_builder_job
-    return if status != 'available'
+    return unless should_enqueue_response_builder?
 
     Captain::Documents::ResponseBuilderJob.perform_later(self)
   end
 
   def should_enqueue_response_builder?
-    # Only enqueue when status changes to available
-    # Avoid re-enqueueing when metadata is updated by the job itself
-    saved_change_to_status? && status == 'available'
+    return false if destroyed?
+    return false unless available?
+
+    return saved_change_to_status? if pdf_document?
+
+    (saved_change_to_content? || saved_change_to_status?) && content.present?
   end
 
   def update_document_usage

spec/enterprise/jobs/captain/inbox_pending_conversations_resolution_job_spec.rb

@@ -1,8 +1,6 @@
 require 'rails_helper'
 
 RSpec.describe Captain::InboxPendingConversationsResolutionJob, type: :job do
-  include ActiveJob::TestHelper
-
   let!(:inbox) { create(:inbox) }
 
   let!(:resolvable_pending_conversation) { create(:conversation, inbox: inbox, last_activity_at: 2.hours.ago, status: :pending) }
@@ -14,6 +12,7 @@ RSpec.describe Captain::InboxPendingConversationsResolutionJob, type: :job do
   before do
     create(:captain_inbox, inbox: inbox, captain_assistant: captain_assistant)
     stub_const('Limits::BULK_ACTIONS_LIMIT', 2)
+    inbox.reload
   end
 
   it 'queues the job' do
@@ -22,7 +21,7 @@ RSpec.describe Captain::InboxPendingConversationsResolutionJob, type: :job do
   end
 
   it 'resolves only the eligible pending conversations' do
-    perform_enqueued_jobs { described_class.perform_later(inbox) }
+    described_class.perform_now(inbox)
 
     expect(resolvable_pending_conversation.reload.status).to eq('resolved')
     expect(recent_pending_conversation.reload.status).to eq('pending')
@@ -34,7 +33,7 @@ RSpec.describe Captain::InboxPendingConversationsResolutionJob, type: :job do
     captain_assistant.update!(config: { 'resolution_message' => custom_message })
 
     expect do
-      perform_enqueued_jobs { described_class.perform_later(inbox) }
+      described_class.perform_now(inbox)
     end.to change { resolvable_pending_conversation.messages.outgoing.reload.count }.by(1)
 
     outgoing_message = resolvable_pending_conversation.messages.outgoing.last
@@ -44,7 +43,7 @@ RSpec.describe Captain::InboxPendingConversationsResolutionJob, type: :job do
   it 'creates an outgoing message with default auto resolution message if not configured' do
     captain_assistant.update!(config: {})
 
-    perform_enqueued_jobs { described_class.perform_later(inbox) }
+    described_class.perform_now(inbox)
     outgoing_message = resolvable_pending_conversation.messages.outgoing.last
     expect(outgoing_message.content).to eq(
       I18n.t('conversations.activity.auto_resolution_message')
@@ -52,11 +51,17 @@ RSpec.describe Captain::InboxPendingConversationsResolutionJob, type: :job do
   end
 
   it 'adds the correct activity message after resolution by Captain' do
-    perform_enqueued_jobs { described_class.perform_later(inbox) }
-    activity_message = resolvable_pending_conversation.messages.activity.last
-    expect(activity_message).not_to be_nil
-    expect(activity_message.content).to eq(
-      I18n.t('conversations.activity.captain.resolved', user_name: captain_assistant.name)
-    )
+    described_class.perform_now(inbox)
+    expected_content = I18n.t('conversations.activity.captain.resolved', user_name: captain_assistant.name)
+    expect(Conversations::ActivityMessageJob)
+      .to have_been_enqueued.with(
+        resolvable_pending_conversation,
+        {
+          account_id: resolvable_pending_conversation.account_id,
+          inbox_id: resolvable_pending_conversation.inbox_id,
+          message_type: :activity,
+          content: expected_content
+        }
+      )
   end
 end

spec/enterprise/models/captain/document_spec.rb

@@ -82,4 +82,161 @@ RSpec.describe Captain::Document, type: :model do
       end
     end
   end
+
+  describe 'response builder job callback' do
+    before { clear_enqueued_jobs }
+
+    describe 'non-PDF documents' do
+      it 'enqueues when created with available status and content' do
+        expect do
+          create(:captain_document, assistant: assistant, account: account, status: :available)
+        end.to have_enqueued_job(Captain::Documents::ResponseBuilderJob)
+      end
+
+      it 'does not enqueue when created available without content' do
+        expect do
+          create(:captain_document, assistant: assistant, account: account, status: :available, content: nil)
+        end.not_to have_enqueued_job(Captain::Documents::ResponseBuilderJob)
+      end
+
+      it 'enqueues when status transitions to available with existing content' do
+        document = create(:captain_document, assistant: assistant, account: account, status: :in_progress)
+
+        expect do
+          document.update!(status: :available)
+        end.to have_enqueued_job(Captain::Documents::ResponseBuilderJob)
+      end
+
+      it 'does not enqueue when status transitions to available without content' do
+        document = create(
+          :captain_document,
+          assistant: assistant,
+          account: account,
+          status: :in_progress,
+          content: nil
+        )
+
+        expect do
+          document.update!(status: :available)
+        end.not_to have_enqueued_job(Captain::Documents::ResponseBuilderJob)
+      end
+
+      it 'enqueues when content is populated on an available document' do
+        document = create(
+          :captain_document,
+          assistant: assistant,
+          account: account,
+          status: :available,
+          content: nil
+        )
+        clear_enqueued_jobs
+
+        expect do
+          document.update!(content: 'Fresh content from crawl')
+        end.to have_enqueued_job(Captain::Documents::ResponseBuilderJob)
+      end
+
+      it 'enqueues when content changes on an available document' do
+        document = create(
+          :captain_document,
+          assistant: assistant,
+          account: account,
+          status: :available,
+          content: 'Initial content'
+        )
+        clear_enqueued_jobs
+
+        expect do
+          document.update!(content: 'Updated crawl content')
+        end.to have_enqueued_job(Captain::Documents::ResponseBuilderJob)
+      end
+
+      it 'does not enqueue when content is cleared on an available document' do
+        document = create(
+          :captain_document,
+          assistant: assistant,
+          account: account,
+          status: :available,
+          content: 'Initial content'
+        )
+        clear_enqueued_jobs
+
+        expect do
+          document.update!(content: nil)
+        end.not_to have_enqueued_job(Captain::Documents::ResponseBuilderJob)
+      end
+
+      it 'does not enqueue for metadata-only updates' do
+        document = create(:captain_document, assistant: assistant, account: account, status: :available)
+        clear_enqueued_jobs
+
+        expect do
+          document.update!(metadata: { 'title' => 'Updated Again' })
+        end.not_to have_enqueued_job(Captain::Documents::ResponseBuilderJob)
+      end
+
+      it 'does not enqueue while document remains in progress' do
+        document = create(:captain_document, assistant: assistant, account: account, status: :in_progress)
+
+        expect do
+          document.update!(metadata: { 'title' => 'Updated' })
+        end.not_to have_enqueued_job(Captain::Documents::ResponseBuilderJob)
+      end
+    end
+
+    describe 'PDF documents' do
+      def build_pdf_document(status:, content:)
+        build(
+          :captain_document,
+          assistant: assistant,
+          account: account,
+          status: status,
+          content: content
+        ).tap do |doc|
+          doc.pdf_file.attach(
+            io: StringIO.new('PDF content'),
+            filename: 'sample.pdf',
+            content_type: 'application/pdf'
+          )
+        end
+      end
+
+      it 'enqueues when created available without content' do
+        document = build_pdf_document(status: :available, content: nil)
+
+        expect do
+          document.save!
+        end.to have_enqueued_job(Captain::Documents::ResponseBuilderJob)
+      end
+
+      it 'enqueues when status transitions to available' do
+        document = build_pdf_document(status: :in_progress, content: nil)
+        document.save!
+        clear_enqueued_jobs
+
+        expect do
+          document.update!(status: :available)
+        end.to have_enqueued_job(Captain::Documents::ResponseBuilderJob)
+      end
+
+      it 'does not enqueue when content updates without status change' do
+        document = build_pdf_document(status: :available, content: nil)
+        document.save!
+        clear_enqueued_jobs
+
+        expect do
+          document.update!(content: 'Extracted PDF text')
+        end.not_to have_enqueued_job(Captain::Documents::ResponseBuilderJob)
+      end
+    end
+
+    it 'does not enqueue when the document is destroyed' do
+      document = create(:captain_document, assistant: assistant, account: account, status: :available)
+      clear_enqueued_jobs
+
+      expect do
+        document.destroy!
+      end.not_to have_enqueued_job(Captain::Documents::ResponseBuilderJob)
+    end
+  end
 end

spec/jobs/conversation_reply_email_job_spec.rb

@@ -0,0 +1,33 @@
+require 'rails_helper'
+
+RSpec.describe ConversationReplyEmailJob, type: :job do
+  let(:conversation) { create(:conversation) }
+  let(:mailer) { double }
+  let(:mailer_action) { double }
+
+  before do
+    allow(Conversation).to receive(:find).and_return(conversation)
+    allow(ConversationReplyMailer).to receive(:with).and_return(mailer)
+    allow(mailer).to receive(:reply_with_summary).and_return(mailer_action)
+    allow(mailer).to receive(:reply_without_summary).and_return(mailer_action)
+    allow(mailer_action).to receive(:deliver_later).and_return(true)
+  end
+
+  it 'enqueues on mailers queue' do
+    ActiveJob::Base.queue_adapter = :test
+    expect do
+      described_class.perform_later(conversation.id, 123)
+    end.to have_enqueued_job(described_class).on_queue('mailers')
+  end
+
+  it 'calls reply_with_summary when last incoming message was not email' do
+    described_class.perform_now(conversation.id, 123)
+    expect(mailer).to have_received(:reply_with_summary)
+  end
+
+  it 'calls reply_without_summary when last incoming message was email' do
+    create(:message, conversation: conversation, message_type: :incoming, content_type: 'incoming_email')
+    described_class.perform_now(conversation.id, 123)
+    expect(mailer).to have_received(:reply_without_summary)
+  end
+end

spec/models/message_spec.rb

@@ -327,14 +327,11 @@ RSpec.describe Message do
         message.conversation.contact.update!(email: 'test@example.com')
         message.message_type = 'outgoing'
 
-        # Perform jobs inline to test full integration
-        perform_enqueued_jobs do
-          message.save!
+        ActiveJob::Base.queue_adapter = :test
+        allow(Redis::Alfred).to receive(:set).and_return(true)
+        perform_enqueued_jobs(only: SendReplyJob) do
+          expect { message.save! }.to have_enqueued_job(ConversationReplyEmailJob).with(message.conversation.id, kind_of(Integer)).on_queue('mailers')
         end
-
-        # Verify the email worker is eventually scheduled through the service
-        jobs_for_conversation_count = ConversationReplyEmailWorker.jobs.count { |job| job['args'].first == message.conversation.id }
-        expect(jobs_for_conversation_count).to eq(1)
       end
 
       it 'does not schedule email for website channel if continuity is disabled' do
@@ -345,15 +342,8 @@ RSpec.describe Message do
         message.conversation.contact.update!(email: 'test@example.com')
         message.message_type = 'outgoing'
 
-        initial_job_count = ConversationReplyEmailWorker.jobs.count { |job| job['args'].first == message.conversation.id }
-
-        perform_enqueued_jobs do
-          message.save!
-        end
-
-        # No new jobs should be scheduled for this conversation
-        jobs_for_conversation_count = ConversationReplyEmailWorker.jobs.count { |job| job['args'].first == message.conversation.id }
-        expect(jobs_for_conversation_count).to eq(initial_job_count)
+        ActiveJob::Base.queue_adapter = :test
+        expect { message.save! }.not_to have_enqueued_job(ConversationReplyEmailJob)
       end
 
       it 'does not schedule email for private notes' do
@@ -363,15 +353,8 @@ RSpec.describe Message do
         message.private = true
         message.message_type = 'outgoing'
 
-        initial_job_count = ConversationReplyEmailWorker.jobs.count { |job| job['args'].first == message.conversation.id }
-
-        perform_enqueued_jobs do
-          message.save!
-        end
-
-        # No new jobs should be scheduled for this conversation
-        jobs_for_conversation_count = ConversationReplyEmailWorker.jobs.count { |job| job['args'].first == message.conversation.id }
-        expect(jobs_for_conversation_count).to eq(initial_job_count)
+        ActiveJob::Base.queue_adapter = :test
+        expect { message.save! }.not_to have_enqueued_job(ConversationReplyEmailJob)
       end
 
       it 'calls SendReplyJob for all channels' do

spec/services/messages/send_email_notification_service_spec.rb

@@ -14,17 +14,11 @@ describe Messages::SendEmailNotificationService do
       before do
         conversation.contact.update!(email: 'test@example.com')
         allow(Redis::Alfred).to receive(:set).and_return(true)
-        allow(ConversationReplyEmailWorker).to receive(:perform_in)
+        ActiveJob::Base.queue_adapter = :test
       end
 
-      it 'schedules ConversationReplyEmailWorker' do
-        service.perform
-
-        expect(ConversationReplyEmailWorker).to have_received(:perform_in).with(
-          2.minutes,
-          conversation.id,
-          message.id
-        )
+      it 'enqueues ConversationReplyEmailJob' do
+        expect { service.perform }.to have_enqueued_job(ConversationReplyEmailJob).with(conversation.id, message.id).on_queue('mailers')
       end
 
       it 'atomically sets redis key to prevent duplicate emails' do
@@ -40,10 +34,8 @@ describe Messages::SendEmailNotificationService do
           allow(Redis::Alfred).to receive(:set).and_return(false)
         end
 
-        it 'does not schedule worker' do
-          service.perform
-
-          expect(ConversationReplyEmailWorker).not_to have_received(:perform_in)
+        it 'does not enqueue job' do
+          expect { service.perform }.not_to have_enqueued_job(ConversationReplyEmailJob)
         end
 
         it 'attempts atomic set once' do
@@ -62,7 +54,7 @@ describe Messages::SendEmailNotificationService do
         conversation.contact.update!(email: 'test@example.com')
       end
 
-      it 'prevents duplicate workers under race conditions' do
+      it 'prevents duplicate jobs under race conditions' do
         # Create 5 threads that simultaneously try to enqueue workers for the same conversation
         threads = Array.new(5) do
           Thread.new do
@@ -73,24 +65,24 @@ describe Messages::SendEmailNotificationService do
 
         threads.each(&:join)
 
-        # Only ONE worker should be scheduled despite 5 concurrent attempts
-        jobs_for_conversation = ConversationReplyEmailWorker.jobs.select { |job| job['args'].first == conversation.id }
+        # Only ONE job should be scheduled despite 5 concurrent attempts
+        jobs_for_conversation = ActiveJob::Base.queue_adapter.enqueued_jobs.select do |job|
+          job[:job] == ConversationReplyEmailJob && job[:args].first == conversation.id
+        end
         expect(jobs_for_conversation.size).to eq(1)
       end
     end
 
     context 'when email notification should not be sent' do
       before do
-        allow(ConversationReplyEmailWorker).to receive(:perform_in)
+        ActiveJob::Base.queue_adapter = :test
       end
 
       context 'when message is not email notifiable' do
         let(:message) { create(:message, conversation: conversation, message_type: 'incoming') }
 
-        it 'does not schedule worker' do
-          service.perform
-
-          expect(ConversationReplyEmailWorker).not_to have_received(:perform_in)
+        it 'does not enqueue job' do
+          expect { service.perform }.not_to have_enqueued_job(ConversationReplyEmailJob)
         end
       end
 
@@ -102,10 +94,8 @@ describe Messages::SendEmailNotificationService do
           conversation.contact.update!(email: nil)
         end
 
-        it 'does not schedule worker' do
-          service.perform
-
-          expect(ConversationReplyEmailWorker).not_to have_received(:perform_in)
+        it 'does not enqueue job' do
+          expect { service.perform }.not_to have_enqueued_job(ConversationReplyEmailJob)
         end
       end
 
@@ -117,10 +107,8 @@ describe Messages::SendEmailNotificationService do
           conversation.contact.update!(email: 'test@example.com')
         end
 
-        it 'does not schedule worker' do
-          service.perform
-
-          expect(ConversationReplyEmailWorker).not_to have_received(:perform_in)
+        it 'does not enqueue job' do
+          expect { service.perform }.not_to have_enqueued_job(ConversationReplyEmailJob)
         end
       end
     end

spec/workers/conversation_reply_email_worker_spec.rb

@@ -1,46 +0,0 @@
-require 'rails_helper'
-
-Sidekiq::Testing.fake!
-RSpec.describe ConversationReplyEmailWorker, type: :worker do
-  let(:conversation) { build(:conversation, display_id: nil) }
-  let(:message) { build(:message, conversation: conversation, content_type: 'incoming_email', inbox: conversation.inbox) }
-  let(:mailer) { double }
-  let(:mailer_action) { double }
-
-  describe 'testing ConversationSummaryEmailWorker' do
-    before do
-      conversation.save!
-      allow(Conversation).to receive(:find).and_return(conversation)
-      allow(ConversationReplyMailer).to receive(:with).and_return(mailer)
-      allow(ConversationReplyMailer).to receive(:with).and_return(mailer)
-      allow(mailer).to receive(:reply_with_summary).and_return(mailer_action)
-      allow(mailer).to receive(:reply_without_summary).and_return(mailer_action)
-      allow(mailer_action).to receive(:deliver_later).and_return(true)
-    end
-
-    it 'worker jobs are enqueued in the mailers queue' do
-      described_class.perform_async
-      expect(described_class.queue).to eq(:mailers)
-    end
-
-    it 'goes into the jobs array for testing environment' do
-      expect do
-        described_class.perform_async
-      end.to change(described_class.jobs, :size).by(1)
-      described_class.new.perform(1, message.id)
-    end
-
-    context 'with actions performed by the worker' do
-      it 'calls ConversationSummaryMailer#reply_with_summary when last incoming message was not email' do
-        described_class.new.perform(1, message.id)
-        expect(mailer).to have_received(:reply_with_summary)
-      end
-
-      it 'calls ConversationSummaryMailer#reply_without_summary when last incoming message was from email' do
-        message.save!
-        described_class.new.perform(1, message.id)
-        expect(mailer).to have_received(:reply_without_summary)
-      end
-    end
-  end
-end