Outlook Out of Office not working on any device

Dear @Steve Bore,

Good day! Welcome to Microsoft Q&A forum!

Regarding this matter, to better understand the situation, could you please help clarify the following:

• When you enable Out of Office, does it remain enabled, or does it turn itself off?
• Are internal and external senders both not receiving the automatic reply?
• If someone sends you a test email while Out of Office is enabled, do they receive any bounce-back message or simply no automatic response?
• Have you tested the Out of Office setting through Outlook on the web (https://outlook.office.com), and does it show as enabled there as well?

Also, I noticed you mentioned that you've already tried everything within your capacity and knowledge. To help avoid suggesting steps you've already completed, could you share some of the troubleshooting you've tried so far and whether you encountered any errors or unexpected behavior along the way?

As a quick verification, if you haven't already done so, you could try to:

• Sign in to Outlook on the web and confirm that Automatic Replies is enabled there
• Send a test email from a different email account
• Ask a colleague or another external sender to perform a test and confirm whether they receive the automatic reply

Your confirmation would be very helpful in ensuring you receive the most suitable support!

If you’re able to share a bit more about your situation, I might be able to suggest some helpful next steps. 

Kindly let me know when there are updates or if you need further assistance. Any updates you’re able to share would be really helpful.

I appreciate your time and look forward to hearing how things are going!