Issue

Outlook rule that performs action “have server reply using a specific message” doesn’t work properly. The reply gets delivered for internal senders, but never reaches external senders. Email server is running Microsoft Exchange 2010.

Resolution

Automatic replies to external senders via Outlook rules by default is disabled in Exchange 2010. To enable this:

1. Open Exchange Management Console
2. Navigate to Organization Configuration > Hub Transport > Remote Domains > Default > Properties
3. In Message Format tab enable “Allow automatic replies“
4. Save changes

Microsoft Exchange 2010
Outlook 2016