(Optional) On macOS, you can add -K option to the ssh-add command to store passphrases in your keychain. Set the permissions for all files in ~/.ssh to 600 $ chmod 600 ~/.ssh. If you don’t have the original ppk key. On macOS Sierra and later, you need to create the config file in ~/.ssh/ with the following text: Copy your id_rsa.pub key to your server’s .ssh/authorized_keys file. Now only the user itself has access to .ssh and .ssh/authorized_keys in which the public keys of your remote machines are stored. I had the SSH key’s password stored in the macOS Keychain, and if I manually ran ssh-add -K /path/to/private/key it would load the key without asking me to input a password, proving that they key… The command is the same for adding, changing, and removing a SSH private key passphrase: ssh-keygen -p. After entering this command, you’ll be asked for the private key that you want to edit. Next we want to add the key to the keychain. ... ssh-add-K mynewkey. Hit Enter to edit the id_rsa private key. > Now SSH authentication should works fine, but you need to run “ssh-add -A” after each logout/login OR just add “ssh-add -A” in your rc script to load the keys. Alternatively you can use a key without a passphrase… Thankfully, the solution is pretty simple. The problem was that macOS kept asking for the SSH passphrase when connecting to them, which kind of defeats the purpose of using Public Key authentication in the first place. Adding, Changing, or Removing a Passphrase from Your SSH Private Key. Add your passphrase to your keychain using this command: $ ssh-add -K (you will see Enter passphrase for [your system]/.ssh/id_rsa: ) Solution no. The behavior of ssh, ssh-agent and ssh-add, changed in macOS Sierra.There is no GUI pop up asking for ssh key passphrase to store the identity in ssh-agent.Instead, ssh asks you for the passphrase via command line prompt, then stores the passphrase in the Keychain. If you don’t know what that means, then … > You can add the old keys to the keychain by entering “ssh-add -K ” again. When adding your SSH key to the agent, use the default macOS ssh-add command, and not an application installed by macports , homebrew , or some other external source. My Problem. A workaround for this is to add a passphrase to the key temporarily: ssh-keygen -p -f ~/.ssh/id_rsa # when prompted, input a temporary password Next, add the key to the agent (and Keychain) using ssh-add -K. Then, remove the passphrase from the key: ssh-keygen -p -f ~/.ssh/id_rsa # when prompted for a new passphrase, … It prompts for the passphrase and saves them to the keychain. If you are using macOS, and after verifying that your new key allows you to connect, you have the option of storing the passphrase for your key in the macOS keychain. Add that key to the key chain. Add your passphrase to your keychain using this command: $ ssh-add -K (you will see Enter passphrase for [your system]/.ssh/id_rsa: ) Choose a name for this key and optionally add a passphrase to it. The ppk is generated specifically for putty. Tell macOS Sierra to stop Keychaining ssh key passphrase. Whether you already have a config file for your .ssh folder or … in ~/.ssh/config add the following to the end of the file, to allow usage of the Apple Keychain for SSH: Copy your id_rsa.pub key to your server’s .ssh/authorized_keys file. Before adding a new SSH key to the ssh-agent to manage your keys, you should have checked for existing SSH keys and generated a new SSH key. On OSX Sierra and later, you also need to configure SSH to always use the keychain (see Step 2 below). Using macOS 10.15, attempting to automatically load a password protected SSH key into ssh-agent by using the SSH configuration option UseKeychain was not working. 2: The mac is looking for a .pem key. 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