diff --git a/enterprise/app/services/enterprise/message_templates/hook_execution_service.rb b/enterprise/app/services/enterprise/message_templates/hook_execution_service.rb
index 17515b628..92ccba553 100644
--- a/enterprise/app/services/enterprise/message_templates/hook_execution_service.rb
+++ b/enterprise/app/services/enterprise/message_templates/hook_execution_service.rb
@@ -2,6 +2,7 @@ module Enterprise::MessageTemplates::HookExecutionService
   def trigger_templates
     super
     return unless should_process_captain_response?
+    return perform_handoff unless inbox.captain_active?
 
     Captain::Conversation::ResponseBuilderJob.perform_later(
       conversation,
@@ -10,6 +11,19 @@ module Enterprise::MessageTemplates::HookExecutionService
   end
 
   def should_process_captain_response?
-    conversation.pending? && message.incoming? && inbox.captain_active?
+    conversation.pending? && message.incoming? && inbox.captain_assistant.present?
+  end
+
+  def perform_handoff
+    return unless conversation.pending?
+
+    Rails.logger.info("Captain limit exceeded, performing handoff mid-conversation for conversation: #{conversation.id}")
+    conversation.messages.create!(
+      message_type: :outgoing,
+      account_id: conversation.account.id,
+      inbox_id: conversation.inbox.id,
+      content: 'Transferring to another agent for further assistance.'
+    )
+    conversation.bot_handoff!
   end
 end