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This question is Cygwin-specific.

My intention is to SSH to Linux Debian 9 Stretch server from Windows 10 Pro client.

Steps I have done so far:

  1. Installed Cygwin with OpenSSH package.

  2. Generated private-public pair in Cygwin:

    ssh-keygen -t rsa -b 8192

  3. Copied the server's public key to Cygwin:

    ssh-copy-id user_name@ip_address -p port_number

  4. First time connected to the server:

    ssh user_name@ip_address -p port_number

    It told me:

    The authenticity of host '[ip_address]:port_number ([ip_address]:port_number)' can't be established.

    ... Are you sure you want to continue connecting (yes/no)?

    I replied yes.

  5. I defined an alias in Cygwin and got it sourced:

    vi .bash_aliases

    Exactly the same as the first time connection.

  6. I restarted Cygwin.

  7. Now the issue I'm having, is that when I do:

    ssh-server

    It always asks me for password to private key. And I don't know why. Because it's encrypted obviously, but how do I get rid of it?:

    Enter passphrase for key '/home/user_name/.ssh/id_rsa':

Note: When connecting from my Linux machine, it does not ask for that password. Did I miss a step?

EDIT:

  1. When I start SSH Agent and add the key, I can connect flawlessly:

    • Start SSH Agent:

      eval `ssh-agent -s`

    • Add missing keys to identity: 

      ssh-add

But this only works for a session, why is it not permanent?

Vlastimil Burián
  • 4,376

1 Answers1

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As an unencrypted private key is not an option for me, I must have set a passphrase. I hoped there's some trick that would unlock my key upon login. But as it appears, that is not going to happen.

So I retreated for the solution when Cygwin asks for my password always upon launch.

You can use whatever editor installed, I used nano, to edit your startup file, e.g.:

nano .bashrc

Simply add these two lines to the end of the file:

eval `ssh-agent -s`
ssh-add

You can find more information about ssh-agent in the manual, the same goes for the ssh-add.

Now, every time you start your Cygwin terminal, it will ask you for password to the private key.

Vlastimil Burián
  • 4,376