Using Classic Outlook on Windows for personal email, calendar, and contact management
I had the same issue, but I managed to fix it.
On Outlook application, go to File > Office Account, check whether your affected email address is signed in under Account (on the left side).
If it is not, then try click Switch account and check whether your affected email address account is there.
Most likely it is not, just add and sign in and it should be fixed.
You can switch back to your original account after you added the affected email address account.