SSH on Mac keeps asking for the private key password
If you have come here because of a dialog that keeps showing up each time you attempt to ssh on mac with or without a passphrase, maybe this will help you. Issue: I generated a public / private key without a passphrase using the putty key gen on windows. Copied id_rsa.pub and id_rsa.ppk to ~/.ssh directory on my Mac Ran the below command ssh -i id_rsa.ppk xxx@xx.xx.xx.xx I kept getting the dialog asking for the password. After three attempts, it would terminate with a permission denied error. Failed attempts: Attempt 1: Renamed id_rsa.ppk to id_rsa Ran the below commands chmod 600 id_rsa ssh -i id_rsa xxx@xx.xx.xx.xx Attempt 2: Renamed id_rsa.ppk to id_rsa Ran the below commands chmod 600 id_rsa sudo ssh -i id_rsa xxx@xx.xx.xx.xx and more... Successful attempts: Download puttygen.exe Import (Conversions -> Import Key) the private key id_rsa.ppk Click Conversions -> Export OpenSSH Key Save as id_rsa.pem Copy id_rsa.pem to ~/.ssh. You sho...