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I have not been able to save my ssh passphrase to the keychain since upgrading to MacOS Sierra. I understand how to use the ssh-add -K flag and the UseKeychain configuration option, and my coworkers use them without any problems. My .ssh/config contains this:

Host *
    AddKeysToAgent yes
    UseKeychain yes

However, I cannot seem to save the passphrase to keychain, even if I explicitly use ssh-add -K! The agent always asks for a passphrase when it’s empty, and ssh-add -A does not add any keys. How can I troubleshoot this?

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    I have had this same problem with every single MacOS installation after Sierra. I don't understand what it might be that is messing this up. No amount of googling turns up anything besides "ssh-add -K". :( – Ezku Dec 21 '18 at 13:55

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