Well, I can't believe Outlook365 is not used by Mac users (as a Windows user, I never had big issues with that software).
If you want a real Mac issue for which I had a hard (and long, like 4 years) time to get the correct answer, here is one: I brought an iMac from Canada (sorry, I'm Canadian) with a QWERTY keyboard so I changed it to AZERTY.
When the Mac was booting up, although I had carefully made sure my preferences had been changed to French AZERTY, the system didn't care and always started as a QWERTY (once you were successfully logged in, it was working)... Imagine my sorrow to discover that after I had changed my password. I even thought someone hacked my iMac, as I couldn't anymore log in!!!
I went to Apple stores and to MacWay stores, and spent numerous hours with the Apple support to not prevail: no one understood how to solve that issue.
So during 4 years, I had to use simple passwords such as "toto"" as they were good for both QWERTY and AZERTY keyboards... I finally found someone who understood how to solve the issue, after 4 years.