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E.g. from my Windows PC I connect to my personal Ubuntu server via GUI like MobaXterm, in that server I generated the RSA keys and copied it to another remote server so I would be able to connect to that remote server with no password and disable the password access.

So, that remote server is considered safe and secure, it has no password access, but what about my own server that I use to connect to that remote server with no password?

Is it like, a never ending chain, initial server will always has SSH password access in order to be able to continue connecting through it to passwordless servers?

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You can set up key-based authentication from your Windows PC to your personal local server, of course you need to be able to access your server to do this.
This will involve a password whether that's through an initial SSH session to set up the keys and disallow password SSH login, or whether you log in by entering the password in a physical console type of setup (attaching a monitor and keyboard to your personal server).

Once keys are set up, the only point you have to enter a password is at the client end, in this case when you're logging into your windows PC.

Obviously problems occur if you lose keys to a server that you cannot physically access and you don't have any other way to authenticate yourself.

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