What looked at first like a simple task – turned out to cost me hours of trial and error.

Some of the problems I’ve encountered:

• Cygwin’s SSHd, OpenSSH and CopSSH all work great on Windows EC2 instances. Until you try to bundle an instance. After you launch a bundled instance – the SSHd service wouldn’t run, because of permissions problems – and throws weird error messages in the different logs.
• It turned out that Sysprep was responsible for this – mangling the permissions of the SSHd users.
• Turning Sysprep off as suggested in some places sounds like a recipe for problems down the road.
• Couldn’t find the source code of an SSHd implemented in Java, and FreeSSHd. Wouldn’t be smart to use closed-source applications for this, security wise…
• Couldn’t find any other SSHd client, or a full solution for this specific problem.

I Googled everywhere, until I assembled the solution which consists of:

• Installing Cygwin’s SSHd (thank you LifeHacker).
• AutoExNT service is used to run a batch file right after the machine’s launch (Thank you Microsoft).
• Update_Cygwin solved the permissions problem (Thank you VCL).

So, the steps to SSH into a Windows machine on Amazon EC2 are these:

• Install Cygwin, make sure you include the OpenSSH package.
• chmod +r /etc/passwd
• chmod +r /etc/group
• chmod 755 /var
• ssh-host-config
• Choose root as the name of the privileged account.
• Copy your public key into the authorized_keys file of the account you’d like to log-in with.
• Install the AutoExNT service.
• Run the update_cygwin script right after each instance launch.
• Don’t forget to open the SSH port on the security group of the instance.

I still don’t understand:

1. How come Windows doesn’t come pre-configured with an SSHd service. What do people use in order to administer Windows Server machines? Unsecure Telnet? Do they all use Remote Desktop for this?? Very weird…
2. How come there’s no solution for this already on Amazon EC2 forums? Saw lots of people run into this problem, and it seems like pretty basic stuff. I guess that Windows Server administration still isn’t that popular…

Thanks for everybody on the forum that saved me valuable time getting this problem behind me…

Now for the real work

This entry was posted on Friday, May 29th, 2009 at 4:33 pm and is filed under Uncategorized. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.