Q&A: Sending an Automated Vacation Reply With Outlook.com Is it possible to set up a vacation bounce-back message in Outook.com Webmail? Outlook.com, Microsoft's successor to its old Hotmail service, does let you set up an automated reply to people who send you e-mail when you are away. To set up a vacation message, log into your Outlook.com account and click the gear-shaped settings icon on the right side of the mailbox screen. Choose "More mail settings" from the menu. When you land on the Options screen, go to the "Managing your account" area and click "Sending automated vacation replies." On the Vacation Reply screen, click the button next to "Send vacation replies to people who e-mail me" and compose the bounce message you would like your correspondents to receive as your reply. Outlook.com gives you the choice of sending the reply to everyone who e-mails you, or just to people on your Contacts list. Unless you regularly get mail from people you do not already have in your address book, you may want to just send the bounce message to known contacts and avoid confirming your currently active e-mail address to spammers. When you have set up your message, click the Save button to activate the vacation reply. People who send you frequent messages will get your automated reply once every four days to remind them that you are still on vacation, but Outlook.com skips replying to mail filtered into the Junk folder. When you return from your trip, retrace your steps back to the Vacation Reply screen and click the button next to "Don't send any vacation replies." Click the Save button to turn off the bounce message until your next break.