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I need to frequently login to many machines but I can only login to them from a proxy machine or using an SSH tunnel (by tunneling through that proxy machine). The problem is that I cannot use authorized_keys on the proxy machine, therefore I need to enter the password every time I setup the tunnel.

How can I automate it? I was thinking about combining expect with some way to enter the password automatically without having to store it openly.

I am using Linux on all of the machines mentioned.

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How about using agent forwarding?

You can enable it in /etc/ssh/ssh_config (or ~/.ssh/config):

Host *
ForwardAgent yes

or add "-A" every time you connect to your proxy: ssh -A user@remote_host

By enabling this, you allow your proxy to forward your key to your target machines, so you can freely connect to other machines.

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