Using older versions of Outlook for Mac in business environments
FWIW, I was doing some poking around today and here are some tidbits I found. This may explain why Outlook is having issues. It seems there are a lot of changes going on at Microsoft right now and perhaps support for Yahoo mail has fallen by the wayside? I didn't see anything in the May 23rd Mac update below that would be causing an issue, but in the May 16 update they introduced Outlook Profiles. This was a few days before I started having/noticing issues, even though I'm running a much older version of Outlook. I'm guessing something has to be changing behind the scenes to support these new features that may be breaking older versions as well?
In case you're curious about the new Outlook Profiles feature, I included a link to that as well. I believe it is only available if you are using the "New Outlook", not the "Legacy View". I'm not a fan of the New Outlook and don't use it at home, but my work computer started up with it automatically after the last update even though it was previously set to Legacy View.
I also saw an article where the Windows version of the Outlook app is also being updated to be more in line with the web version. At the time of the article (April 5, 2023) it only supported Microsoft accounts and Gmail, but not other third-party email services. Those are in the works. Could possibly be the same with the Mac release? That would explain why my Exchange account was unaffected, but my AOL and Yahoo accounts were.
Outlook Release notes
May 23, 2023
Version 16.73.1 (Build 23052000) Resolved issuesOutlook
- Mail: Fixed an issue where the undo button in toast is not clickable.
- Search: Fixed a highlighting issue for the first search suggestion.
- Calendar: Fixed an issue where calendars become unchecked in some cases after restarting the app.
May 16, 2023 Version 16.73 (Build 23051401) Feature updatesOutlook
- Introducing Outlook Profiles: For a much-improved multi-account experience within Outlook.
- Support for Aliases: Your Outlook account's additional email addresses can now be used to send emails.
- Folder Item Count: The total number of items in a folder can now be seen by right-clicking the folder name.
Resolved issuesOutlook
- Fixed a crash that occurs when setting calendar sharing permissions.
- Fixed an issue with applying default sensitivity label to mail and calendar items.
- Fixed an issue where events more than one year in the future don't appear on the calendar.
- Fixed a calendar issue where two event compose windows are shown when opening room finder from the event compose popover.
- Fixed an authentication issue with IMAP and iCloud Accounts.
Profiles in Outlook for Mac
https://insider.microsoft365.com/en-us/blog/profiles-in-outlook-for-mac
Outlook for Windows Article