Add warning for unsent Signal groups messages.

packages/zammad-addon-bridge/src/app/controllers/channels_cdr_signal_controller.rb

@@ -458,6 +458,36 @@ class ChannelsCdrSignalController < ApplicationController
 
     Rails.logger.info "Signal group member #{member_phone} joined group #{params[:group_id]} for ticket #{ticket.id}"
 
+    # Check if any articles had a group_not_joined notification and add resolution note
+    # Only add resolution note if we previously notified about the delivery issue
+    articles_with_pending_notification = Ticket::Article.where(ticket_id: ticket.id)
+                                                        .where("preferences LIKE ?", "%group_not_joined_note_added: true%")
+
+    if articles_with_pending_notification.exists?
+      # Check if we already added a resolution note for this ticket
+      resolution_note_exists = Ticket::Article.where(ticket_id: ticket.id)
+                                              .where("preferences LIKE ?", "%group_joined_resolution: true%")
+                                              .exists?
+
+      unless resolution_note_exists
+        Ticket::Article.create(
+          ticket_id:     ticket.id,
+          content_type:  'text/plain',
+          body:          'Recipient has now joined the Signal group. Pending messages will be delivered shortly.',
+          internal:      true,
+          sender:        Ticket::Article::Sender.find_by(name: 'System'),
+          type:          Ticket::Article::Type.find_by(name: 'note'),
+          preferences:   {
+            delivery_message:        true,
+            group_joined_resolution: true,
+          },
+          updated_by_id: 1,
+          created_by_id: 1,
+        )
+        Rails.logger.info "Ticket ##{ticket.number}: Added resolution note about customer joining Signal group"
+      end
+    end
+
     render json: {
       success: true,
       ticket_id: ticket.id,

packages/zammad-addon-bridge/src/app/jobs/communicate_cdr_signal_job.rb

@@ -40,10 +40,37 @@ class CommunicateCdrSignalJob < ApplicationJob
     if is_group_chat && group_joined == false
       Rails.logger.info "Ticket ##{ticket.number}: User hasn't joined Signal group yet, skipping message delivery"
 
+      # Track group_not_joined retry attempts separately
+      article.preferences['group_not_joined_retry'] ||= 0
+      article.preferences['group_not_joined_retry'] += 1
+
       # Mark article as pending delivery
       article.preferences['delivery_status'] = 'pending'
       article.preferences['delivery_status_message'] = 'Waiting for user to join Signal group'
       article.preferences['delivery_status_date'] = Time.zone.now
+
+      # After 3 failed attempts, add a note to inform the agent (only once)
+      if article.preferences['group_not_joined_retry'] == 3 && !article.preferences['group_not_joined_note_added']
+        Ticket::Article.create(
+          ticket_id:     ticket.id,
+          content_type:  'text/plain',
+          body:          'Unable to send Signal message: Recipient has not yet joined the Signal group. ' \
+                         'The message will be delivered automatically once they accept the group invitation.',
+          internal:      true,
+          sender:        Ticket::Article::Sender.find_by(name: 'System'),
+          type:          Ticket::Article::Type.find_by(name: 'note'),
+          preferences:   {
+            delivery_article_id_related:   article.id,
+            delivery_message:              true,
+            group_not_joined_notification: true,
+          },
+          updated_by_id: 1,
+          created_by_id: 1,
+        )
+        article.preferences['group_not_joined_note_added'] = true
+        Rails.logger.info "Ticket ##{ticket.number}: Added notification note about pending group join"
+      end
+
       article.save!
 
       # Retry later when user might have joined