Outlook for Mac (Paid Version) – Dozens of Challenges, Any Suggestions?

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.

Here is the doc submitted to MS:

Subject: Escalation Request – Outlook for Mac Issues

Dear Microsoft Support,

First, I kindly request that this case be assigned to an agent with full Outlook for Mac expertise. So far, most of the agents I have spoken/dealt with seem more Windows-focused or not fully trained in Outlook for Mac.

Important Notes Before Troubleshooting

• Pleasedo not suggest reinstalling Outlook or switching back to Legacy without addressing the risks outlined below.
• I havenine IMAP accounts (no POP accounts). When I previously followed support advice to create a new identity and reinstall Outlook, I lost all reminders and address book entries. I only managed to recover them by restoring from Time-Machine. This was unacceptable and must not happen again.
• If reverting to Legacy is necessary, I need aclear guarantee that no emails, reminders, or contacts will be lost. 
• The reason I initially left Legacy was because of persistent folder duplication (e.g., folders named xx17 and higher) and your agent said this would be a good solution. Unless there is a permanent fix for this, reverting is not a viable option.

Enclosure: Detailed Issue List – Outlook for Mac (Office 365, Commercial)

A. Data Loss Risks & Backup

B. Search & Synchronization

C. Email Functionality & UI

D. Calendar, Contacts & Reminders

E. Notifications, Updates & Misc.

F. Support Experience & Compensation

Request for Resolution and Compensation

Given the number and persistence of these issues, Outlook for Mac (Commercial) feels under-tested and unstable despite being a paid product. I have already spent more than 20 hours waiting for promised calls, writing follow-up emails, dealing with answers that regress, non-Mac trained agents, bad copy-paste answers, attempts by agents to close unresolved issue, and troubleshooting without resolution to name a few.  I feel like an unpaid and poorly treated beta tester!

I request:

1. Escalation to an Outlook for Mac expert.
2. Clear guidance on safe backup/recovery for contacts, reminders, and accounts.
3. A statement on how I can requestcompensation for this buggy application, the time spend and the ongoing headaches it gives, to name a few. Maybe the easiest is to cancel the need to pay the licencing fees.  Please confirm the appropriate channel for submitting this claim unless you are authorised to so immediately, which I hope for simplicity’s sake you are.

Thank you for your attention. I look forward to your prompt and constructive response.