How do I configure freeSSHd on Windows Server 2008 so I can log in using ssh?

Posted by Daryl Spitzer on Server Fault See other posts from Server Fault or by Daryl Spitzer
Published on 2009-09-14T19:45:11Z Indexed on 2010/05/01 19:39 UTC
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I've installed freeSSHd on a Windows Server 2008 box (following the instructions in How to install an SSH Server in Windows Server 2008), including:

  • created a user named "dspitzer" with NTLM authorization
  • opened an exception for port 22 in the Windows Firewall

But when I try to connect (from a Mac OS X 10.5.8 command-line), I get permission denied after entering the password:

$ ssh 12.34.56.78
[email protected]'s password: 
Permission denied, please try again.
[email protected]'s password: 
Permission denied, please try again.
[email protected]'s password: 
Received disconnect from 12.34.56.78: 2: Too many attempts.

I've also tried:

$ ssh [email protected]
[email protected]'s password: 
Permission denied, please try again.
[email protected]'s password: 
Permission denied, please try again.
[email protected]'s password: 
Received disconnect from 12.34.56.78: 2: Too many attempts.

I've also tried changing the authorization to "Password stored as SHA1 hash" and entering a simple password, but I get the same problem. And I've tried a different user name ("Administrator") with no luck.

I've confirmed that I am connecting to the server I'm configuring—if I stop freeSSHd and try to connect I get:

$ ssh 12.34.56.78
ssh: connect to host 12.34.56.78 port 22: Operation timed out

I get the exact same results from a Linux command-line.

Any advice or troubleshooting tips?

Update: I tried disabling the firewall (in response to geeklin's comment) and it made no difference.

Update #2: I no longer have this machine (I've changed employers), so I have no way of verifying the answers. I guess all I can do is make this question "community wiki".

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