How to send recurring auto response messages in Outlook 2019 / 365/ 2016 when out of office?

Last Updated: October 2019

Applicability: Office 365 / 2019, 2016, 2013. Windows and macOS.

Here’s a question we got from Dorothy:

Hello! i work as a travel agent and my availability is of utmost important to my customers. Every now and then, i am away from office due to vacations, and i would like to ensure my customers are aware of that and stuff doesn’t fall through the cracks. In the past, I used to work for a company, and i remember that there was a trick to set an out of the office auto-responder there. I now work from home and use and Gmail on Microsoft Outlook 2019, is there a way to setup an out of the office rule to notify others that i am away?

Thanks for your good question and good luck with your new business.

You can easily define auto reply texts when out of the office using Rules. In this tutorial we’ll explain how to do that in Windows and then in the macOS. Readers can put this in practice in order to have Outlook reply automatically in case they are away for vacation, or any other leave of absence.

For completeness we have added a short section on how to use Outlook on Exchange to send OOTO replies.

Setting Auto replies on Windows

Using Rules

If you are using Gmail or Hotmail/ on Outlook, you’ll need to use Rules to setup your autoresponder.

Please proceed as following:

  • Open Outlook.
  • First off, define an Outlook message template that will be sent when absent. This post has all information you need to setup your template.
  • Next, in the Email tab, hit on the Rules button.
  • Select Manage Rules and Alerts.
  • The Rules Wizard will open up.
  • Hit the New Rule… button
  • Then select Apply rules on emails i receive.


  • Hit Next.
  • Specify is you would like to have this out of the office rule apply to specific emails.
  • Hit Next if you want the rule to apply to all incoming messages.
  • Now  check the Reply using a specific template rule.
  • In the lower pane hit the specific template link.


  • Browse your computer for the email template you defined in the first step of this tutorial.
  • Note: The templates are saved as oft files.

Select a Reply Template

  • Once found your template, highlight it and hit Open.
  • Hit Next.
  • Define any exceptions to your rule as needed.
  • Hit Next.
  • Provide your rule a meaningful name, as shown below


  • When done, hit Finish.
Deactivating rules

Note: Please remember that you’ll need to deactivate your rules when back from your vacations or leave of absence; otherwise your automatic emails will continue to be sent.

If you want to disable your replies, proceed as following:

  • Open Outlook
  • Hit Rules
  • Hit Manage Rules and Alerts
  • Uncheck any rules that you would like to deactivate.


  • When done, hit Apply.

Using Exchange

If your company is using an Exchange Server, then the configuration process is very simple:

  • Open Outlook.
  • Hit File.
  • Now hit the Automatic Replies button (note that you’ll need to be connected to Exchange to set those up).
  • Now define your auto reply for senders inside an outside your organization.
  • Hit OK when done.

Out of the office replies on MAC

If you are on macOS then the process is fairly simple, here are the steps:

  1. Open Outlook for macOS
  2. From the upper bar, navigate to Tools and ten choose Rules.
  3. The Rules dialog will open up.
  4. If you are using Gmail or, highlight IMAP in your left hand side.
  5. Hit on the + sign at the bottom of the dialog.
  6. Define your Rule name:



  1. In the Do the Following section select Reply and then hit the Reply Text… button.
  2. Now go ahead and define your out of the office reply text as shown below



  1. When done, hit OK.
  2. Check the “Do not Apply” and “Enabled” boxes and hit OK. Once back from your vacation remember to uncheck the Enabled button to deactivate the rule.
  3. You’ll rules dialog will look as following. Every incoming email will be automatically responded by Outlook.



More readers questions

Multiple auto replies for one mailbox

We were asked whether you are able to set different automatic responders according to who sent the message. That’s possible,as the Outlook Rules Wizrd allows you to condition your email messages by several parameters:

  • by people,
  • whether you are in the TO or CC,
  • whether you are the sole recipient
  • Whether specific words show up in the subject or body
  • By email importance

Rule_Wizard_Outlook_2019 - Outlook

In order to use multiple replies, all you need to do is build different rules and then assign different Outlook reply templates to each.

How do i know if my auto replies were sent?

Good question, you’ll see your replies showing up as entries in your Outlook sent items folder

Does it work when my PC is off?

This is a very important question – the answer is that the rules you are defining in Outlook are client only, meaning that they will run only when Outlook is running. This is not the case if you are using autoreplies on Outlook on Exchange.

Can i setup an Auto-Forward instead?

When on PTO / vacation/ holidays or while travelling,  you might choose to automatically forward your emails to other people so they are able to respond. You can use the Rules Wizard to define a specific rule to handle that.

Can i add a picture to my auto reply message?

On Windows, you are able to add rich text information to your replies, be it links, pictures and even animated gifs. You can also add your signature to all outgoing emails.


In case of any additional questions, feel free to let us know. Hope it Helps!


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