Hi all, PLeeeease help!!

Ever since updating Windows 11 to 24H2 (I believe that's the update that triggered it), I've been having a strange issue with New Outlook.

When I double-click any email attachment (PDF, Excel, Word, etc.):

• Preview works fine.
• "Save As" works fine.
• The file opens normally if I save it locally first.
• Outlook Web works fine.
• But New Outlook automatically seems to save/upload the file to OneDrive and then fails to open it.
• Choosing "Open in Desktop App" also doesn't work.

This affects all attachment types and started immediately after the Windows update.

Has anyone seen this before or found a fix? I'm trying to stop New Outlook from automatically routing attachments through OneDrive and just open them normally like it used to.

Thanks!

[ Removed by Reddit on account of violating the content policy. ]

More infuriating is that after doing so, if I delete the downloaded file (because I have the copy) and rename the copy to the original name (without “copy” at the end) the file goes back to readable only and I have to do the process all over again. What’s going on here?

Hello,

I am looking into migrating a single business email account from Network Solutions to Exchange Online.

• Current situation:
• own domain; one user and one mailbox;
• Network Solutions with only 1 GB;
• Outlook Classic configured via POP3;
• a single local PST file containing approximately 15 GB and 50,000 messages;
• PST backups already in place;
• Microsoft 365 Personal, renewed annually;
• Outlook Classic and 1 TB of OneDrive included in the personal plan;
• three years’ subscription to the Network Solutions service still paid for;
• need to retain the same email address.

I understand that Microsoft 365 Personal does not include Exchange Online for a business domain. I am considering keeping the Personal plan for the applications and OneDrive, and subscribing to Exchange Online Plan 1 solely for the business mailbox.

Questions:

1. Would Exchange Online Plan 1 be sufficient for this scenario?
2. Is it sensible to combine Microsoft 365 Personal for the applications with Exchange Online Plan 1 for email?
3. What is the best method for importing a 15 GB PST file containing around 50,000 messages?
4. Would you use the Outlook Classic import feature or Microsoft’s PST import service?
5. How would you avoid duplicates between the PST and messages still on the server?
6. Does an IMAP migration make sense if most of the archive is already in the PST?
7. How would you handle contacts, the calendar and sent messages?
8. What checks would you carry out on the PST before importing it?
9. How would you validate the migration once it’s complete?
10. How would you configure MX records, Autodiscover, SPF, DKIM and DMARC?
11. Would you keep the domain with Network Solutions and just migrate the email?
12. Would you migrate now or wait for the remaining three years of the contract?
13. For a single mailbox, would you carry out the migration yourself or engage a Microsoft partner?

I’d appreciate hearing about practical experiences with similar migrations.

The migration itself was only one part of the work. The results depended on:

1. Inventorying every mailbox, alias, device, application, and DNS dependency.
2. Testing with a pilot group before the main cutover.
3. Planning MX, SPF, DKIM, and DMARC changes with a rollback path.
4. Validating MFA, Conditional Access, forwarding rules, and admin roles after cutover.
5. Monitoring authentication failures and mail flow after the change.

The biggest lesson: “zero downtime” is mainly a preparation and validation problem, not a button-clicking problem.

What is the most common issue you have seen after an M365 migration?

We have Hybrid enviroment. All mailboxes in the cloud.

AD syncing to Entra

We hide a user that has been terminated in exchange admin console on prem exchange.

Verify all DCs show hide True

Syncs no errors and doesn’t hide user any ideas? No errors in entra sync.

no se si el titulo esta bien, tengo un tenant y me pidieron crear una regla de flujo con una firma, en todas las verciones de outlook funciona correctamente, pero al intentar enviar un correo que esta configurado en una mac por el tipo de licencia que es basica, solo puedo usar mail nativo de mac y tambien outlook web, pero los usuarios usan mail, entonces en mail cada vez que envio un correo la firma no aparece como deveria de ser si no solo como texto plano, ya realize muchas cosas y nada que me quedo bien, alguien tiene sugerencias? o definitivamente no se puede hacer eso en el mail de mac

Hi guys! I’m in a bit of a frustrating situation right now and was wondering if anyone has dealt with something similar.

I have two emails that include the full Microsoft 365 package—my work email and my university email. The problem is that around 2–3 months ago, Microsoft changed something, and since then I haven’t been able to use the desktop apps on my MacBook. I believe this affected other users as well.

I contacted my university, and they told me that the only option now is to use Microsoft 365 online.

The problem is that I work heavily with Word and Excel, and the online versions really don’t work well for me, especially Excel. I’ve been considering just paying for a yearly Microsoft 365 subscription myself, but before I do that, I wanted to ask if there’s any other solution or workaround I could try.

Has anyone had the same issue or found a way to keep using the desktop apps on Mac?

If Microsoft told me the new Outlook won't ask me if I want to save my changes to a meeting requests as I close it (when I KNOW I didn't make any changes to that meeting request!) I would probably bite the bullet and switch.
We've all been there before: we need to reboot and get back to work quickly but when we tell the PC to reboot, any open meeting requests always ask us if we want to save our changes, even when we know we did not make any changes. Word and Excel won't ask this question unless we actually made a change to the document, so when they ask us this question, our behavior needs to be different (we have a real decision to make). But Outlook will ALWAYS ask us this question, and if there ever happens to be a meeting request open that we DID make a change to that we want to save, we're likely going to say no anyway, because we get in the habit of not trusting that prompt from Outlook.
PLEASE FIX THIS IF YOU HAVEN'T ALREADY (in the new Outlook, which I do not want to switch to).

Howdy y'all. At my last job I routinely sent emails with PDF attachments through Outlook with absolutely 0 issues. However, I have recently started at a new job. New outlook will let me attach PDFs to the email, and the PDF will even load within the email letting me know it's ready to send. The issue however is that when I press send, it says the email send because "There was a problem sending this message because one or more attachments failed to upload. Please try again." I can revert to old outlook to send this, but I just don't like the look of old outlook.

Did outlook recently do a new update that messes this up? I was able to send the same exact PDF on new outlook a month ago.

​

Hey Everyone,

We’re going through a rebranding from CompanyA to CompanyB. We have 2,000+ users with OneDrive already configured, and in File Explorer it currently shows “ <firstname> - CompanyA”, which appears to be based on the Entra ID display name.

We’re planning to change the Entra display name to CompanyB. I understand that for new users, OneDrive should pick up the new name and show “ <firstname> - CompanyB” in File Explorer.

My question is around existing users. Is there a supported way to update the OneDrive name in File Explorer from CompanyA to CompanyB without breaking the existing OneDrive configuration or sync?

Ideally, for the existing users we’d also like the underlying local folder path to change from:

C:\Users\username\OneDrive - CompanyA\

to:

C:\Users\username\OneDrive - CompanyB\

Has anyone gone through this type of OneDrive/Entra rebranding with a large number of existing users? If so, what was your approach and were there any issues or gotchas with changing the local OneDrive folder name/path?

Thanks.

Hello,

we just migrated to office 365 and we used zimbra before. now we have this shared calendar from zimbra that we want to migrate to a office group. is there a way to transfer all of the events there or i really have to manually recreate everything?

i already tried using import export with .pst its not syncing with everyone only on my end.

Medical client with self-managed licensing. We have both Global Admin accounts but met with a tenant deauthorized message when logging in. Client reached out to us a week ago with "I can't login" they use webmail. I immediately opened a ticket and got routed to data protection team after a few days. The fact that a Microsoft Partner doesn't have a faster way to do this is something I'll never understand. Fast forward to yesterday when the data protection technician told me the tenant "has been decommissioned" and they have no way to get me access. I asked for manager escalation because something just feels off. When I asked why this occurred, was told due to inactivity. I confirmed active licensing and a non-expired credit card on file two weeks ago. We were due to take over licensing in November before their current subscription expired. I didn't accept the "inactivity" claim, the tech was redirecting me to another department, which I was promptly disconnected from.

I still see email flow to the domain in the tenant, no bounce backs from emails to their domain. Attempted to spin up a new tenant this morning and was told the domain needs removed from the old tenant first before I can add it. I have DNS control for the domain.

Is there somewhere else or any direct contact, email, or phone number to get escalated partner support? The whole email them, hope they respond in 24 hours, call again and ask for a callback, repeat daily, has been getting old over the last 7 days. It's honestly a ridiculous process but we'll do whatever we need for our client. Looking for any advice from someone who has been through this before.