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I've configured Cygwin's sshd to run on a Windows Server 2008 machine.

I am able to log in to ssh fine, however once I'm logged in, I am unable to make any outgoing network connections out of the session (e.g. connect via SQL*Plus, or other network-based utilities). Note that I am able to use these applications with no issues when logged in via a simple bash (i.e. non-ssh) terminal, so it is not (exclusively) a firewall issue.

I am not using private-key password-less login, as this was causing all kinds of issues with share permissions. I've also tried turning off privilege-separation, but that does not help.

Not sure if it is relevant, but I log in to this machine via RDP exclusively (in fact it's firewalled to hell). The reason I'm using sshd is so I can create (truly) detached sessions using screen, since I'd been having problems with RDP killing my long-running jobs. My proposed workflow was to be: log in via RDP, open an ssh session, use screen, run my job, C-A C-D to detach, log out of RDP, come back later to check on the job via a new ssh session, screen -RR to reattach.

Any help would be greatly appreciated!


This is the process I followed to get sshd up and running:

  1. Install cygwin & openssh.
  2. Configure sshd (as admin, run ssh-host-config -y)
  3. Start sshd


  • Windows Server: 2008 R2 Enterprise
  • Cygwin: setup.exe Version 2.774
  • sshd: OpenSSH_6.1p1, OpenSSL 1.0.1c 10 May 2012
share|improve this question
We're probably gonna need some more data if you can get it. What error message do you get when you try to ssh to another server from within the session? Also, is there any info in /var/log/sshd.log –  Costa Feb 5 '13 at 22:34
The machine is firewalled: inbound except TCP-3389 (RDP) and outbound except to two databases (an Oracle DB on TCP-1521 and a MSSQL on TCP-1433), so I can't connect to any other ssh servers, however the issue is that I cannot connect to the databases from an SSH session (initiated as: ssh user@localhost). I don't get any error message, but within the ssh session, connections to the DBs (e.g. via SQL*Plus) timeout. The same connection (via cmd.exe or non-ssh bash) works fine from the box. Nothing particular in the sshd log. –  Josh Bode Feb 6 '13 at 3:07

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