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is there anyway to do a passwordless logon using cygwin for ssh sessions? More precisely does anyone know of any guide or suggestion how can i configure to use cygwin with sshpass utility like we have on ubuntu?

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you can use the same utilities to set up passwordless key authentication as from ubuntu. the procedure should be exactly the same (ssh-keygen to generate keys, copy the pub key to server and add it to .ssh/authorized_keys). if you do have a passphrase for your key, then you can use ssh agent to forward your credentials, etc.

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