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MacOS recently solved this "issue".

When rebooting a FileVault encrypted machine, where it normally "hangs" asking for a user to unlock it, you can now SSH into the machine, but instead of getting a prompt it interprets your SSH login as a user logging in, hangs up, and proceeds to booting up.

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Huuuh, is this true? Where is the Apple docs for this? Recently tried to setup a headless macos machine and all my searching led me to either having to do autologin or disabling FileVaukt fully.

https://news.ycombinator.com/item?id=45294440

The good news: macOS can unlock FDE over SSH.

The bad news: `The capability to unlock the data volume over SSH appeared in macOS 26 Tahoe.`

The "bad news" about Tahoe is largely overblown unless you hang out in the control center (or whatever they call that notification area) all day, which is the only place you'll actually notice Liquid Glass on a Mac.

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