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After Sierra update, a new bug was found where ssh-agent no longer remembers the passphrase for keys added. Not surprised by their answer, Apple stated TL;DR: is not a bug, but a feature.

Many threads I've read revolves around using ssh-agent -A/-K but the problem is not the loading, but that I never wrote my passphrase down anywhere.

What do I do now? Can I retrieve my passphrase from Keychain?

PD: The reason I don't know my passphrase is the whole point of the setup was not to write down a passphrase but let keychain manage it in order to centralize passwords, as I followed some best practiced (I think it was GitHub's?) where they mentioned "using easy to remember passphrases are easy to crack; using random letters/number/symbols are hard to remember so you most likely will write it down, which is also insecure. The solution is letting keychain manage it" or something like that.

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Nevermind, I just found this Leaving this open in case anybody panic as I did.

Steps:

  1. Open Keychain
  2. Search for "SSH"
  3. Double click on the SSH file you want
  4. Select Show password on the bottom-left corner
  5. Unlock your keychain with the administrative password.