How to set up recurring Out of Office auto-reply for certain days of the week in Outlook 2016

Out of Office recurring auto-reply for certain days of the week in Outlook

How to set up recurring Out of Office auto-reply for certain days of the week in Outlook 2016.

In the event of you being away, you can use Out of Office to show people who email you that you’re loving life abroad, or you may only work several days of the week and need to find a way to automate your messages.

Unfortunately, Microsoft hasn’t been able to add this into their systems as of yet, however, there are ways around this! (Microsoft… please add.)

The way we’re doing this is with the rules within Outlook. It should work 100% of the time as long as the headers are all correct with the rules. If you have a better way to do this let us know! Let’s get into it.


Step 1: Open Outlook, head over to the ‘Home’ tab, and press ‘Rules’. Once in, go to ‘Manage Rules and Alerts’.

Out of Office Rules

Setting up Rules within Outlook

Step 2: Select “New Rule”.

Settting Rules and Alerts for Out of Office

Setting up Rules and Alerts with New Rule

Step 3: Select the option within the list “Apply rule on messages I receive”. This is under the category “Start from a blank rule”. Once selected, click next.

Outlook Rules Wizard Out of Office

Setting up Office 365 Rules Wizard

Step 4: Tick the box that has “with specific words in the message header”.

Office 365 Rules Wizard for Specific Words

Office 365 Rules Wizard for Specific Words

Step 5: Once ticked and selected, under the list, you should see “Apply this rule after the message arrives with specific words in the message header.”. If you click the underlined “specific words”, this will bring up another menu. In this box, you can type in the abbreviation for the day of the week you want this to apply to, for example, we used ‘Friday’ and for the word we want to filter by is ‘Fri’. Once done, click add and then okay.

Step 5

Step 6: Once you’ve clicked OK, it will take you back to the previous screen. You can just hit “Next” to go to the next screen.

Step 7: The next screen looks very much like the above, however, it does have a few differences. In this new list, select “have server reply using a specific message”. Again, similar to Step 5, at the bottom, you have the option to select ‘a specific message’ doing so, will bring up a new option to enter your Out of Office message, just how you normally would. Once completed, just hit ‘Save & Close’.

Step 7

Step 8: After completing the above step, you will be taken back to the same window. You can make sure everything looks okay by clicking the underlined blue text in the ‘Step 2’ section at the bottom. Once confirmed, just hit ‘Next’.

Step 9: In the next stage, you are given the option to select any exceptions. In most cases, this won’t be needed however you can take a look through them and see what’s in them should you want to select any. Once confirmed, you can just hit next.

Step 9

Step 10: Now you’re on the final screen of the rule, you can review your rule again and make sure everything is looking good. Once confirmed, make sure to hit the ‘Turn on this rule’ and name it something that you like. This bit doesn’t matter!

Step 10

Step 11: Once confirmed, all emails that have your day (for us it’s Friday) will have ‘Fri’ in its header and this rule sends the Out of Office on receipt of that email.

Did this help you? Let us know and we’ll help you!

Want to know more about Office 365 and it’s capabilities?

You can find out more on the Office 365 forum and maybe something in our Software section.


  1. Maud Gubler Reply


    It didn’t work for me. When I click on “a specific message”, an empty New email window opens. Do I have to fill something in the recipient section ? I have just written my message in the body section so far.

    1. Brandon Kilmosoa Post author Reply

      You normally don’t have to put anything in the recipeient section. You should just be able to add in what you want in the main body section, and click save – and anyone emailing in should recieve that same message.

  2. Jack Smith Reply

    Just so others don’t have the same issues with it.

    Make sure to Place spaces around the abbreviation. Such as ‘ mon ‘ or you will have issues when someone like ‘montana’ or ‘solomon’ email you and the rule sees mon in the header.


    1. lyelaaah Reply

      I hope adding the space before and after solves my problem because when I tried this hack, Outlook was randomly sending out my autoreply on days other than the one specified.

  3. Jo Reply

    This was very useful, thank you very much.
    Surely it would be easier for Microsoft to add in a calendar to create these rules though??!!

  4. Teresa Melia Reply

    I’ve tried this and thought it was working, but my out of office message was sent on a Tuesday, when it’s set up for Friday! I will try it again with the spaces around ‘ Fri ‘ as suggested above! Hope it works

  5. pg Reply

    Good attempt at a real solution, but, there may be issues with this as if you get sent a chain of emails, this may read info from the other headers? and could then reply in unexpected ways, just be careful, you don’t want to get into the dreaded email loop of death! 😎

  6. Kim Phillips Reply

    Wish there was a calendar function, similar to setting up reoccurring meetings. Set this for Friday, and there is no option to do every other Friday (bi-weekly)

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