Search Knowledge Base: How do I set up a vacation message/autoreply in Outlook for Mac? To set up a vacation message/autoreply in Outlook 2011: Go to the Tools menu and select Out of Office. Select Send Out of Office messages and configure the settings as desired. You have the option to set it for specific dates and have seperate messages for senders outside of the organization. This will send the automatic reply only once to a sender. When finished, click OK. Need more help?