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. 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… Add that key to the key chain. 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. On OSX Sierra and later, you also need to configure SSH to always use the keychain (see Step 2 below). Alternatively you can use a key without a passphrase… 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. It prompts for the passphrase and saves them to the keychain. On OSX, the native ssh-add client has a special argument to save the private key's passphrase in the OSX keychain, which means that your normal login will unlock it for use with ssh. 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. Whether you already have a config file for your .ssh folder or … Set the permissions for all files in ~/.ssh to 600 $ chmod 600 ~/.ssh. 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, … Copy your id_rsa.pub key to your server’s .ssh/authorized_keys file. ... ssh-add-K mynewkey. If you don’t have the original ppk key. 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. Tell macOS Sierra to stop Keychaining ssh key passphrase. Hit Enter to edit the id_rsa private key. (Optional) On macOS, you can add -K option to the ssh-add command to store passphrases in your keychain. Choose a name for this key and optionally add a passphrase to it. Copy your id_rsa.pub key to your server’s .ssh/authorized_keys file. My Problem. 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. Adding, Changing, or Removing a Passphrase from Your SSH Private Key. 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. Add your passphrase to your keychain using this command: $ ssh-add -K (you will see Enter passphrase for [your system]/.ssh/id_rsa: ) > 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. Store the passphrase in the macOS keychain. > You can add the old keys to the keychain by entering “ssh-add -K ” again. 2: The mac is looking for a .pem key. Now only the user itself has access to .ssh and .ssh/authorized_keys in which the public keys of your remote machines are stored. Add or edit the macOS .ssh config file so it always picks up the SSH key even across restarts. Next we want to add the key to the keychain. If you don’t know what that means, then … One of the Mac’s best features for tech types has been disabled by default in Sierra: being able to save the passphrase for an SSH public-private key pair in the macOS keychain. 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