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HOW TO: Configure FreeSSHd on Windows 2012 and Connect with Putty

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Recently I started playing around with Chef for a project. Chef needs SSH and setting SSH up on Windows is something I've not done before. I couldn't find a set of good instructions so here goes.

I used a AWS EC2 Windows 2012 x64 Server and Windows 8 x64 desktop.


  • Install  and configure FreeSSHd on the server
  • Create keys
  • configure Putty to connect to the server

Install FreeSSHd


Configure FreeSSHd

Open FreeSSHd settings (may have to kill the service and start manually to get the GUI).

  • SSH tab:
    • Max number = 2
    • idle = 600
  • Authentication tab
    • Pub key folder = C:\Program Files (x86)\freeSSHd\keys
    • Password auth = disabled
    • Pub key auth = required
  • Users tab
    • add
      • login=chef
      • auth = 'Pub key (ssh only)'
      • user can use = shell
    • click OK
Add firewall rule to allow connection into FreeSSHd

Generate Public and Private keys

  • Open PuttyGen
  • Click ‘Generate’
    • move the mouse pointer around as instructed to generate the key
  • Save a Putty compatible private key
    • Click ‘Save private key’
    • Save this to the client PC, Putty will need this
    • You should really save with a passphrase for extra security
  • Save OpenSSL compatible private key for Chef knife
    • ‘Conversions’ menu > ‘Export OpenSSH Key’ > save as a *.pem
  • Save the public key
    • Copy the contents of ‘Public key for pasting into OpenSSH authorized file:’ and paste into a textfile.
    • rename this file ‘chef’ (no file extension, the filename must match the user login name created above)
    • drop this file into the public key folder C:\Program Files (x86)\freeSSHd\keys on the server.

Connecting with Putty

  • Open Putty (or Putty portable)
  • Enter the IP address of the server
  • Connection type = SSH (obviously!)
  • In the left menu tree
    • Connection > SSH > Auth > ‘Private key file for authentication:’ > click browse
    • Select the private key that was generated above
    • Click ‘Open’
  • when prompted ‘login:’ > enter ‘chef’ > hit enter
  • If the private key was saved with a passphrase then enter this when prompted
  • You should now be connected to the server.
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Janaka Abeywardhana Janaka Abeywardhana


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