I’ve been playing around (in my copious free time 😉 ) with other methods of connecting to and managing Server 2008 Core. One of the things I’ve wanted to do was to be able to SSH directly to Server 2008 Core and have the same command line capability as I do on the console. To that end I did a quick search for similar work and found the following article at TechRepublic about installing an SSH server in Windows 2008. The difference that I wanted to do was to install it in Server Core rather than the full-blown version of 2008.

Like David Davis over at TechRepublic I decided to start with FreeSSHd as my SSH server. The first thing I needed to do was to get it onto the Server Core VM. Rather than downloading it to my desktop and then transferring it to the Server Core VM I decided that would rather download it directly to the Server Core machine. In order to do that I needed wget that would run on Windows. I used the wget binary I downloaded (to my desktop) from Bart Puype in Belgium. Once I copied wget to C:\Windows\System32 I used it download the FreeSSHd.exe binary from FreeSSHd.com.

To install freesshd, just run the freesshd.exe program and it will start up the install wizard. A couple of items to note — on Server Core do not bother with creating a Start Menu item for FreeSSHd and don’t bother with creating a desktop icon either. One of the problems that I encountered when I installed FreeSSHd on Server Core was that I could not configure the SSH server since the task bar icon did not appear on the right (as should be the case since there is no task bar in Server 2008 Core). To configure FreeSSHd I had to edit the freesshdservice.ini file in the C:\Program Files\freesshd directory (the default location for the installation).

A small point to note. Server 2008 Core’s firewall is on by default (even if it’s a domain joined machine) and the policy is to block all inbound connection attempts but to allow outbound connections. After installing FreeSSHd I needed to modify the firewall and decided to use netsh to do so. The command I used was

netsh advfirewall firewall add rule name="SSHd" dir=in action=allow protocol=TCP localport=22

Very simple…I love netsh 🙂

Another problem I ran into was getting the NT authentication to work. I did manage to get the password authentication working but I wanted to tie the FreeSSHd server into the Windows authentication. I’m still not 100% sure as to where the problem lies with the NT authentication integration and will investigate it further.

One of the biggest drawbacks to FreeSSHd is that there is very little (re: almost none) documentation that covers the freesshdservice.ini file. You need to read the forums over at freesshd.com in order to get a sense of what the settings are for the file and what specific changes to the file cause in the overall operation of the server. I hope to get that put together and posted here this summer as I think others will find it useful.

To get the password authentication working I installed FreeSSHd on a Windows Server 2003 system and then created the users I wanted there and copied over the relevant portions of the freesshdservice.ini file to the one on the Server 2008 Core VM. Then, to restart the service I would just issue the commands: net stop freesshdservice and net start freesshdservice and I was good to go. As you can see from the last capture in the gallery below I was able to connect to the server and log in using the account I had created on the Server 2003 system and copied over to the freesshdservice.ini file on the Server 2008 Core VM.

In the future I’m going to try some of the other freely available SSH servers and see if they provide an easier integration into Server 2008 Core.

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