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I'm not sure but t sounds like you generated an ssh key on the remote system and then again on the local system, rather than using the same ssh key pair on both ends.  You need to generate an ssh key and have the private key on the end where Wing is running and the openssh version of the public key on the remote host.In any case, ssh is asking for a passphrase because it hasn't found a matching public key on the remote system (the errors above list where it looked).   See to export a PuttyGen key to openssh format.Note that if you're logging on as root, then the ssh public key needs to go into root's .ssh folder.