I have tried looking all over the place for a solution to load pageant.exe that will load my private keys using their passwords in an automated way and could not find one. Pageant by default knows how to read keys passed as parameters via command line but does not know how to receive the associated passwords belong to them. Therefore, I had created a patched version that knows how to handle the above. Usage: pageant.exe -p file1_password file1.ppk -p file2__password file2.ppk Link to download the patched pageant: pageant.exe Hope that helps.