Using Classic Outlook on Windows for personal email, calendar, and contact management
@Suzanne S Barnhill said
what would happen if you would post your advice as an answer rather than a comment.
This is an Answer and not a Comment.
I tried the mailto link as suggested ... get the same two dialogs [Updating Microsoft 365 and Outlook App Error 0xC0000143] I do NOT get a prompt to choose an app. I checked my default settings, and Outlook (classic) is already selected as the default app.
1 -- One more test to be sure that the problem is opening Outlook with a MailTo command line (this is what happens behind the scenes when you click on a MailTo link)
Open a Windows CMD or Terminal window and execute:
START mailto:"******@mail.com?cc=******@mail.com&subject=MySubject&body=MyBody"
The forum censor will have replaced the user part of the emails with asterisks
2 -- Try an Outlook Repair
https://support.microsoft.com/en-us/office/repair-an-office-application-7821d4b6-7c1d-4205-aa0e-a6b40c5bb88b
3 -- Test with Outlook in Safe Mode (disables all Add-Ins)
https://support.microsoft.com/en-us/office/open-outlook-in-safe-mode-f394c2ee-b2af-e97a-64ee-35cd24414811
4 -- Test with a new Profile
https://support.microsoft.com/en-us/office/create-an-outlook-profile-f544c1ba-3352-4b3b-be0b-8d42a540459d