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

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.

This YouTube video helped http://www.youtube.com/watch?v=lwHktjugAYM

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

Overview

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

Install FreeSSHd

• Download FreeSSHd from http://www.freesshd.com/?ctt=download
• Double click to start installer on the server
• As a service
• Accept all other defaults

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

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.