Issue: Out of Office only responds to senders once, in some instances the OOO needs to send an automatic reply every time

Environment: Microsoft Outlook 365

Resolution: Create a rule within the Out of Office notification


Step 1

In Microsoft Outlook, navigate to the Automatic Replies (Out of Office)


Step 2. 

Start by creating your out of office as normal by setting your date range.  For the 'Inside My Organization' tab, leave the body of the email blank



Step 3.


  • Click on the 'Outside of my Organization) tab, enable 'Auto-reply to people outside my organization'.  
  • Leave the body of the blank. 
  • Click the 'Rules..' button



Step 4. 

Click 'Add Rule...'




Step 5.

  • Enable 'Sent directly to me' and 'Copied (Cc) to me'
  • Enable 'Reply with Template'
  • Click on the 'Template...' button




Step 6. 


  • A new email template will open.  Enter your auto-responder text to the body of the email.  Do not fill out any other fields.
  • Click the 'Save & Close' button



Step 7. 

  • Click 'OK' on the Edit Rules box


  • Click OK on the 'Automatic Reply Rules' dialog box



  • Click OK on the 'Automatic Replies' dialog box




Thats it!  Your out of office automatic reply is set up!