Outlook Calendar and Out of Office Assistant: creating a connection with Zapier

In this case, we want to prevent more work for coming our way in Jira when new vacation events are set up in Outlook.

Go to your Zapier dashboard and fill in the builder as shown below:

  • On the left, select Microsoft Outlook and the New Calendar Event trigger
  • On the right, select Out of Office Assistant for Jira and the Add or Update Absence action
  • Then, click on Try it
  • Next, connect you Outlook account. You can use an existing connection or create a new one

  • Then, you need to select a calendar. We will use a dedicated calendar for vacation entries.

  • Now, go back to Outlook and create an event in the calendar that you have selected

  • Then, you can test the trigger. You should get a result like this:

  • Now it's time to move over to the action to start filling in the details.
  • First, select Add or Update Absence

  • Now, select the connection. If you haven't connected yet to your Out of Office Assistant for Jira account, please use the API Token method as described in the section above.

  • Now it's time to start filling in the details. 
    • Start Date → Start Date Time
    • End Date → End Date Time
    • Message → Body Content. Note that the body content will be automatically stripped from HTML tags and additional formatting so that it reads well in Jira.

  • If you're using a dedicated calendar, then you probably don't need to filter by Event Type. Every new event in that calendar will trigger the zap. But if you're using a general calendar, you can build a filter like this:
    • Event Filter → Subject. This means that the app will look for a matching string in the subject of the Outlook event before accepting it as a valid absence.
    • Event Filter Description. Type here the string that should be matched. It should be broad enough to generate matches but narrow enough to prevent false triggers. In our example, we use "Out of Office". You can also use abbreviations like "OoO", "OoO + username", etc.

Finally, choose the rest of the details in your configuration.

  • Project: In this case, we will select "all projects"
  • Coverer: Select who will be the default assignee instead of you.
  • Mention Type: We will only select to add the "away" label while away
  • Mention Label: Pick what's more relevant to the circumstance. "Away" is the most neutral.

  • Click continue
  • Click on Test to make sure the zap works with the test event that you created
  • Finally, move over to Jira and check that the Out of Office rule is there

How to connect Outlook automatic replies (Out of Office) in Office365

Once your zap has been set up, Outlook Out of Office automatic replies can also be used to trigger a rule in the Out of Office Assistant. In order to do this, automatic replies have to create a calendar block for the period of the absence. This blocked time in the calendar can then be read by Zapier as a new calendar event. 

Let's go step by step:


  • Remember: Your zap connecting Outlook with Out of Office Assistant for Jira must be completed already before creating an Automatic Reply in Outlook with the following steps.
  • This method is possible with Outlook 365. Unfortunately, we haven't been able to find an alternative for the desktop app, either in MacOS or Windows.

Step 1: Access the automatic replies settings

  • In Outlook 365, click on the settings icon and search for "out of office" or "automatic replies"

Step 2: Allow Automatic replies to block time on your Outlook calendar

  • On the Automatic replies screen, you have to enable the following options:
    • Automatic replies on
    • Send replies only during a time period
    • Block my calendar for this period

Step 3: Define the dates and title of the event

If you have mapped the Out of Office Message with the Outlook Event Subject, the title of your automatic reply block will be your message.

  • Next, give a title to the event that is being blocked in the calendar. Make sure to include the Event Filter Description that has been setup in Zapier, as per the instructions above.
    • For example, if the Event Filter Description is "OoO", then the event name can be "OoO - Local Bank Holiday"
  • Check that the Start Time and End Time are accurate
  • Click on Save.

Now, the event will be created on Outlook, thus triggering the Zap.