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Question: Why won't High Sierra honor my auto login setting?

Since I upgraded, every time I close my macbook and reopen it, or shut down and start up, I have to enter my user password.


I have auto login enabled in my settings.


Why is the OS ignoring this and constantly making me re-enter my password?


I'm also really annoyed at now having to maintain separate icloud and os passwords.

MBP 15.4", Mac OS X (10.5.6)

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Question: Why won't High Sierra honor my auto login setting?