Automatically send a vacation reply email from your Hotmail account

The old Hotmail supported "vacation replies", a newer iteration didn't: fortunately, the latest version of Windows Live Hotmail has re-introduced the concept of vacation reply, and implemented even better, as you'll discover in this tutorial. The name says it all: if you use your Hotmail email address for business, or use it every day for important correspondence, you will want to let people know that you are away from the office, on vacation or otherwise: a vacation reply is basically an automatic email that is sent on your behalf, letting know a group of email senders, over which you have control, know that you are currently unavailable, and anything else you care to share!

Setup vacation replies in your Hotmail account

First, sign in to your Hotmail account and go to your inbox. Once there, click on the Options button near the top right corner of the page, and select "More options" from the dropdown: Windows Live will redirect you to the "Hotmail Options" screen.

Under "Managing your account", click on the "Sending automated vacation replies" link at the bottom: (other links not shown on screenshot).
Send automatic vacation replies from your Hotmail account

On the "Vacation reply" screen that loads next, you'll find a text editor quite the same as the one you use to add a signature in Hotmail; just like the signature editor, you can either send a plain text vacation notification, or use "Rich text" (the default, which allows for rich formatting, links, and images in the automated message).

Configure your vacation reply settings

Here's what you'll see on that page; notice that you have two options, with the default (selected) being "Don't send any vacation replies" - in other words, the feature is currently turned off. When vacation reply is disabled, your email senders will not receive a notice, even if you have text currently inside the text editor, as is the case below:
Configure your Hotmail vacation reply settings
To enable this feature, select instead the "Send vacation replies to people who email me" radio button. Then, type the text you want email senders to see in the vacation reply message they'll receive.

Feel free to play around with the standard text formatting options: font family and font size, bold, italic, underline, text alignment, bullets, indents, etc.

Now scroll down to the bottom of the page (depending on your screen resolution, you may not be able to see the final checkbox and Save button).

By default, the "Only reply to contacts" checkbox is checked: we recommend that you leave it checked, as it prevents spammers whose email was not filtered as junk to confirm that your email address is definitely active!

Tip: The exception to this recommendation would come into play if you are using your Hotmail account for business, and are likely to receive messages from prospects (whose email address could of course not be in your contact list / address book).

Once you are done, click on the "Save" button. Your vacation reply is now active: from this point on, anyone in your contacts (or anyone who emails you, if you unchecked that last checkbox), will receive an out-of-office autoreply. Note that to avoid overwhelming your email senders with multiple vacation replies, Hotmail will only send a vacation reply to the same sender every 4 days: if they send you a message on Monday, and several a day the rest of that week, they won't receive another vacation reply until the first email they send you on Thursday.

Disable vacation replies

Once you are back in the office, or want to turn off vacation replies for any reason, follow the steps outlined above: "Options > More options", and click "Sending automated vacation replies". When on that final screen, select "Don't send any vacation replies" and click on the "Save" button. Your vacation reply is turned off!

Tip: since you've already taken the time to create that automated reply, you can leave it inside the editor and Hotmail will remember it. The next time you go on vacations, you can just reactivate the vacation reply without having to re-type it from scratch...