Yeah, I don't think it is the Perl code. It must be the way my /etc/ssh/ssh_config is setup or something.

My test $host has been localhost. I've tried remote hosts as well but same result. When I manually SSH in to localhost, yes I am prompted for a password and yes, it should match the regex /password: ?$/i. I've played around with the regex to try and match anything but then realized the script is not actually getting the prompt, so no matter what I try and match it's not going to work.

The output of the script is:

problem connecting to host: Permission denied (publickey,password,keyb
+oard-interactive)
[download]

Of course, since it didn't manage to receive the password prompt, it never matched the regex.

Thanks for your reply and if you have any suggestions, I look forward to reading them. It's one of those problems that has annoyed me enough to keep me trying stuff until it works :)