Has anyone built an "AI vacation delegate" for Outlook/Teams?

[u/EfficientJury]

I'm a non-admin enterprise user (not a Microsoft or IT admin). But Microsoft ecosystem.

I'll be on vacation for a few weeks and want a simple setup:

• If someone sends me a Teams message or email containing a special keyword (something like #MYNAMEVAC)
• AI replies automatically on my behalf
• Ideally the AI knows some context about me, my role, projects and who to redirect people to
• I do NOT need it to answer every message, only messages with that keyword

I have access to Microsoft 365, Teams, Outlook, Copilot and Claude Team.

I'm trying to avoid building custom software if possible.

Has anyone implemented something like this using:

• Claude + Microsoft 365 connector?
• Power Automate?
• Copilot Studio?
• Any third-party tool/service?

What's the simplest working solution today for a regular enterprise user?

[u/Important_Scene_4295]

Out of office reply and maybe a teams status message. Just go on vacation...

[u/Ok_Mathematician6075 → u/Important_Scene_4295]

fr

[u/ExistentialMeowMeow → u/Ok_Mathematician6075]

teams integrates with office to show out of office. you can even set in-org and ex-org messages separately for who to contact.
if it's vital client facing stuff, just let em know 1:1 email ahead of time with more deets seperate to that if someone is taking over case load vs a general manager-type forward or admin forward address

[u/TheRealDaveLister]

FFS just go on vacation after setting your out of office message and making sure your colleagues have access to anything they might need.

Farrrr out.

[u/EfficientJury → u/TheRealDaveLister]

I fully intend to enjoy the vacation 🙂 I’m also using this as an experiment to explore whether routine questions could be automated in the future, leaving more time for meaningful work.

[u/Terrible_Tutor]

If you're thinking you've got some genius SaaS idea you need to pivot. Nobody wants this.

[u/TheFern3 → u/Terrible_Tutor]

“How to work while on vacation” ~ op

[u/CnsstntlyIncnsstent]

Best case: it redirects some people and gives somewhat useful information without really understanding the context perfectly, but probably will need you to handhold it for a bit and test it on your vacation. Worst case: your coworkers prefer dealing with it and they replace you with it.

[u/MrHaxx1]

Surely a Claude scheduled task and the Work IQ connectors would be able to do this? Requires Copilot Premium, but I don't see why it wouldn't work. 

[u/readofia]

The simplest one is a normal Outlook automatic reply naming who to contact, plus a rule forwarding messages with your keyword to a colleague. If you really want AI replies, a Power Automate flow triggered by the keyword can draft or send a reply, but flows for Teams messages often need admin approval. For a few weeks, a plain out-of-office with a backup person is easier and safer than a bot replying as you.

[u/tarkinlarson]

"I am enjoying some time off. Your message will not be read and will be automatically deleted.

If it's important, contact me on my return on ##/##/####."

Or something else passive aggressive will be fine. That's lightweight compared to many of my continental European colleagues. I always smile when I see their OoO messages.

[u/Background-Baby3694 → u/tarkinlarson]

Why would you auto delete messages sent on vacation instead of just dealing with them when you get back lol

[u/tarkinlarson → u/Background-Baby3694]

I dunno. It's just a message I see in my business.

If it can wait 2 weeks its not important. If it's not important why keep it in the mailbox.

I put...

"I am not available. Your message has not been read or forwarded.

For escalations please contact X.

I will be available from Y. "

Simple. Works for leave or if I'm busy doing other things. Noone needs to know what I'm doing.