diff --git a/app/services/message_templates/hook_execution_service.rb b/app/services/message_templates/hook_execution_service.rb
index 401f90b27..bc161d885 100644
--- a/app/services/message_templates/hook_execution_service.rb
+++ b/app/services/message_templates/hook_execution_service.rb
@@ -25,6 +25,9 @@ class MessageTemplates::HookExecutionService
     return false if conversation.tweet?
     # should not send for outbound messages
     return false unless message.incoming?
+    # prevents sending out-of-office message if an agent has sent a message in last 5 minutes
+    # ensures better UX by not interrupting active conversations at the end of business hours
+    return false if conversation.messages.outgoing.exists?(['created_at > ?', 5.minutes.ago])
 
     inbox.out_of_office? && conversation.messages.today.template.empty? && inbox.out_of_office_message.present?
   end
diff --git a/spec/services/message_templates/hook_execution_service_spec.rb b/spec/services/message_templates/hook_execution_service_spec.rb
index 949d71ac6..9d9d82922 100644
--- a/spec/services/message_templates/hook_execution_service_spec.rb
+++ b/spec/services/message_templates/hook_execution_service_spec.rb
@@ -194,6 +194,25 @@ describe MessageTemplates::HookExecutionService do
       expect(out_of_office_service).to have_received(:perform)
     end
 
+    it 'does not call ::MessageTemplates::Template::OutOfOffice when there are recent outgoing messages' do
+      contact = create(:contact)
+      conversation = create(:conversation, contact: contact)
+
+      conversation.inbox.update(working_hours_enabled: true, out_of_office_message: 'We are out of office')
+      conversation.inbox.working_hours.today.update!(closed_all_day: true)
+
+      create(:message, conversation: conversation, message_type: :outgoing, created_at: 2.minutes.ago)
+
+      out_of_office_service = double
+      allow(MessageTemplates::Template::OutOfOffice).to receive(:new).and_return(out_of_office_service)
+      allow(out_of_office_service).to receive(:perform).and_return(true)
+
+      create(:message, conversation: conversation)
+
+      expect(MessageTemplates::Template::OutOfOffice).not_to have_received(:new)
+      expect(out_of_office_service).not_to have_received(:perform)
+    end
+
     it 'will not calls ::MessageTemplates::Template::OutOfOffice when outgoing message' do
       contact = create(:contact)
       conversation = create(:conversation, contact: contact)