macOS prompting for private ssh key after updating

First, run ssh-add -K and check whether this fixes your problem.

If not:

  • Removed the file and regenerated a new one (must be in ~/.ssh/):
    ssh-keygen -y -f id_rsa >
  • Ensured permissions were set to 600 for both id_rsa and (must be in ~/.ssh/):
    chmod 600 id_rsa*
  • Ran the following command:
    ssh-add -K

After doing this, I was no longer prompted to give my private key password. This appears to actually put the private key password in the correct keychain location for OS X to use.