Hi Shoegazer4,
I understand that you are having issue of not getting password expire notification on Outlook for Mac 2011.
Unfortunately, this feature is not available for Outlook for Mac 2011. We are working on resolving this issue for Mac Outlook.
However, the user will get a password expire notification if they log in to the portal of Office 365 https://portal.microsoftonline.com/.
Thanks,
Yang Yu