Using Classic Outlook on Windows for personal email, calendar, and contact management
Hi Rama D,
Good day.
Hope you are doing well you for posting in Microsoft Community.
To help us narrow down the issue
- Check if your Outlook is in Cached Exchange Mode. If it is, try disabling it and then try deleting the emails again.
- Check if you have any rules set up in Outlook that might be preventing the emails from being deleted. If you do, try disabling them and then try deleting the emails again.
- Try deleting the emails from the Outlook Web App (OWA) instead of the Outlook client application. This will help you determine if the issue is with the client application or the server.
If you are using an Outlook desktop client, please kindly open Outlook in safe mode (Press Windows + R keys > type outlook.exe /safe > click OK) to check a particular situation or result scenario
Please also ask an Office 365 admin to sign in Office 356 admin center, navigate to Exchange admin center > Recipients > Mailbox > choose the affected email account and click Edit > mailbox features > Litigation hold, check if your organization admin enabled Litigation hold on these mailboxes. If Litigation Hold is enabled, the users will be unable to delete emails in their accounts.
I hope this helps let me know if this is contrary to what you need, I would still be helpful to answer more of your questions.
Best Regards
Microsoft Community