And I can't reach my self-hosted mail server in the Outlook desktop app because of this.

For reasons that I cannot fathom, Microsoft wants to act as the relay to my self-hosted e-mail account, if I add the account in Outlook.

> 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

Allegedly, It's so they can use push notifications efficiently from a central place for new mail notifications. Mobile IMAP clients cannot reliably keep a TCP connection open, due to on-device power-management and network management purposes. IMAP natively supports push-based notifications, but mobile networks make that impossible to work reliably.

Because the new Outlook app is actually a web app talking to a Microsoft Web Server that does the actual mail retrieval. This is all clearly explained in their documentation.

When the excellent Windows 10 Mail app was deprecated and they tried to push Outlook that would work through their online services, I switched to Wino Mail (open remake of Windows 10 Mail). My email works.

Surely you can just use another email client to get the email from your self-hosted server right?

This is your own fault for using their BS app.

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.

I’m pretty certain their desktop client applies filters server-side.

I’m pretty certain because my company’s phishing-test emails skip my filters (I assume admins have a “skip filters” toggle). Which, hilariously, makes it even easier to ensure there’s a place that contains only phishing test emails (filter all not on allow-list of domains to one place, filter all on that list to another, ta-da, the main inbox now contains only phishing test emails)

I assume they do the same thing with non-MS email if you use their client, rather than maintain two filter implementations.

All around, yeah, wow, super gross.

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

Why would you self host, then use a client with a dependency like this? Seems like the worst of both worlds.

outlook 2010 works just fine

> 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.

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