Stop Typing Your SSH Passphrase

Every time you reboot, your Mac forgets your SSH key passphrase. Annoying. Here's the fix — takes two minutes.

Tell SSH to use the Keychain

Open ~/.ssh/config and drop this at the very top:

Host *
  AddKeysToAgent yes
  UseKeychain yes

Has to be at the top. SSH reads the file top to bottom and uses the first rule that matches, so if you put it at the bottom it won't do anything.

Add your keys once

Now run this for each key you have:

bash

ssh-add --apple-use-keychain ~/.ssh/id_ed25519
ssh-add --apple-use-keychain ~/.ssh/id_rsa

Enter the passphrase one last time. macOS stores it in Keychain and from now on loads it automatically on login.

Reboot. Done. Never think about it again.

If you sync your dotfiles to a Linux machine, add IgnoreUnknown UseKeychain above the Host * block or you'll get a warning. Linux doesn't know what Keychain is. Can't blame it.