> For reasons that I cannot fathom, Microsoft wants to act as the relay to my self-hosted e-mail account

I can conjecture some reasons. Datamining would be high on the list, since MS can read your mail and thus market to you more effectively. Governments might also be happier if MS can provide them with one-stop access (like Prism) to otherwise self-hosted e-mail accounts proxied through a central server.

"New" Outlook does route all traffic through Microsoft servers. I assume it's so you can get a "unified" mail look on all your devices (phone, etc), but likely a nice source of data mining

outlook 2010 works just fine

This is your own fault for using their BS app.

> For reasons that I cannot fathom

Biggest data heist and most obvious US intelligence operation in human history. I can't fathom why AVs don't treat "Outlook New" as info stealer malware.

Personally, I can't reconcile having a self-hosted email server and using Outlook to access said email.

I'm being an ass in saying this, because I'm aware human motivation is a beautiful kaleidoscope of variables, but I would have guessed at the venn diagram of 'those willing to compromise and use a Microsoft product' is mutually exclusive with that of the 'I'm hardcore enough to self-host email'.

I will say, however, that Outlook used to be one of the better desktop email programs, so I'll grant some legacy lenience.

And I hope all of us have learned a valuable lesson.

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