I don’t think I need to repeat what most of us already know: Microsoft’s in-app Outlook support is incompetent at best, misleading at worst. And so are all other Microsoft channels one can tap in to for support.
• The so-called “experts” loop the same scripted answers, suggest fixes that cause new problems, or simply stop replying.
• Tickets are closed prematurely (likely KPI-driven) without solutions, or left hanging with “we’re still working on it” updates every few weeks. My oldest ticket like this is now in month 4.
• Outlook for Mac feels like a paid beta test, and we are the paying beta testers.

My Mistake (Following Bad Advice)
On the advice of an in-app “expert,” I moved from Classic Outlook to the New Outlook after my IMAP accounts started duplicating files (Title-of-File 28 and so on).


When the New Outlook began breaking down too, I tried switching back. That’s when I lost:
• My entire address book
• All reminders
• Other important data
Now I’m stuck in New Outlook, with Classic no longer an option without risking more loss.

Where I Am Now
• I’ve raised a dozen+ tickets and used the in-app support multiple times (currently broken in my Outllook since months).
• Each time, I asked for a real Mac Outlook expert or higher-level support.
• Instead, I’ve ended up with a list of about two dozen bugs and broken features (which I’ll share separately). I even sent this list with a letter requesting a real expert and a level-two support person.
• The result? A kind but non-expert agent. I ticked the box for email contact (which always results in a phone call), then they want screen sharing, then they offer useless answers, show they did not read thoroughly… and the loop begins again.

My Main Question
Right now, my top priority is:
How can I safely revert back to Classic Outlook without losing data?
• I need a reliable way to back up everything in New Outlook first, so I can restore if things go wrong.
• The backup option in New Outlook is greyed out.
• When I asked support, their advice was literally: “Switch back to Classic and make the backup there.” I know…
• After months of tickets, I still don’t have a safe, confirmed backup/restore method.

Why I’m Posting Here
I no longer trust Microsoft’s “experts.” And I won’t experiment blindly with their suggestions until I know I can restore my data safely.
So I’m asking this community:
• Has anyone successfully reverted from New Outlook to Classic without losing data? And how did you do this?
• How did you back up first?
• Are there tested workarounds for these problems, or is the only realistic option to abandon Outlook for Mac entirely?
Any tested, real-world advice would be much appreciated.

Thanks.

PS and yes, I am on the latest Mac OS and Outlook version.

Attached Files

Outlook Mac Submitted list to MS.pdf (168.2 KB, 0 views)

Cross Posted on reddit/outlook
https://www.reddit.com/r/Outlook/com...of_challenges/

Indeed as I hope for answers here as well as there as different people use different forums.