Sending “Auto Reply” Email Messages

Want to leave your computer for a while without seeming to have disappeared?

Circling ArrowsIf you are a “one-man band” and you want to give yourself the luxury of going on holiday without having to keep up with your emails, then setting an “out of office reply” is the best way of not worrying that your clients and customers think that you’ve disappeared. Home users can do this as well, of course!

What this amounts to is setting something in your email system that triggers an automatic reply when a new email is received. You will still receive the incoming email and you will still be able to check your emails just as you would on any normal day (on your iPad, for instance, while you are sunning yourself). The only difference is that you’ve now warned the recipient not to expect an immediate answer. There’s nothing stopping you from checking your emails just as obsessively as you normally do (!) and there’s nothing stopping you from replying to any of them that you choose to.

The way of setting up “auto replies”, and the flexibility that you have, varies between systems and set-ups. Some possible scenarios are as follows:

  • You have a company email account that runs under Microsoft Exchange Server. In this case, check with the company IT Department to see how to set auto-replies. You can also try the “Out of Office Assistant” in your Outlook Exchange software.
  • You have your own domain name (eg and use its email servers. You probably have access to a web-based control panel that allows you to administer the domain. This control panel will probably have options for setting up an auto-reply.
  • You use Gmail, Yahoo, or some other webmail system. There will be options under the “settings” for setting an auto-reply (see below for Gmail as an example).
  • You use Mail on Mac OSX. You can set an auto-reply by setting a “rule” – see below.
  • You use Microsoft Outlook without Exchange Server. You can build your own auto-reply by combining an email template with a “rule” that you create for incoming messages.
  • You use Microsoft Live Mail. Create your auto-reply message in a text editor (such as Notepad) and build it into a rule created under “Folders” and then “Message Rules”.

Gmail AutoReply Settings
Gmail AutoReply Settings
Depending on your email setup, you may have several ways of setting up an auto-reply. You only need one method, of course, for each incoming email. Note that if you use a method that involves setting up your own email software (eg using “rules”), then your computer must be switched on while you are away as the auto-reply would not, otherwise, be triggered. This doesn’t apply if you are setting an auto-reply either by webmail or by your domain’s control panel.

Mac Mail Rules Box
This is what you want your “Rules” box to look like in Mac Mail
There have been times when I have suggested setting up auto-replies to my computer support clients and they have responded by saying “isn’t it just a good way of telling burglars that you are away?” Realistically, I suppose it might be. If you are worried about this then you must take a view on whether the benefits outweigh the risks and act accordingly. Likewise with the problem of sending auto-replies to spammers. It could be that sending an auto-reply to a spam message that gets into your inbox just confirms to the spammer that your email address is genuine and “live” (thereby increasing the value of your email address to them). Note, though, that some methods of setting up auto-replies allow you to choose whether you reply to everyone or just those email addresses that are in your contact list. This will stop your autoreply from replying to spam messages but it would also mean that any potential new client would think they are being ignored until you manually respond. On balance, I prefer my auto-replies to be sent to too many people rather than too few.

It would be a huge, tedious, blog posting if I went through all of the possibilities in detail, but here’s a couple of examples of setting up auto-replies for two of the most popular methods of using email:

Mac Mail (in Mac OSX)

  • Open Mail
  • Click on the “Mail” command at the top of the screen
  • Click on the “Preferences” option
  • Click on the “Rules” tab
  • Click on “Add Rule”
  • Give the rule a name (such as “AutoReply”)
  • Click on the box that is currently selecting “Any Recipient”
  • Scroll down the list of options and click on “Every Message”
  • Under the section headed “Perform the following actions”, click on the current choice of “Move Message” and scroll down to select the option called “Reply to Message”
  • Click on “Reply message text” and enter the text that you would like the AutoReply to contain.
  • Click on “OK”.
  • The next bit is VERY VERY important! When a box pops up and asks whether you want to apply the rule to selected messages, then click on “Don’t Apply”. If you click on “Apply” you will send unwanted “out of office” messages to emails you have already received!
  • Make sure there is a tick in the box for your new rule that makes it active
  • Close the “Rules” box.

Note that you can not schedule the AutoReply in Mac Mail. You have to turn it on and off manually.

Mac Mail Don't Apply
When you have finished setting up your rule, make sure to click on the “Don’t Apply” button!


  • Log onto your Gmail account (via the web interface)
  • Click on the “Settings” cogwheel at top right
  • Click on the “Settings” option on the menu that has just popped open
  • Scroll down the screen until you find the section headed “Out of Office AutoReply”
  • Complete the form, remembering to click on the “Save” button at the bottom of the page when you have finished.

Note that you can select an option that only sends auto-replies if the sender is in your Gmail contacts list.