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How to set up OpenSSH on Windows

Rob Bruder from Broadband Antenna Tracking Systems shared the steps that he followed to install OpenSSH with FIPS compliant OpenSSL using CYGWIN on a Windows XP machine:

1. Download Cygwin/x from http://cygwin.com/
2. Install it making sure to install the  following packages
   1. Make
   2.  g++ compiler
   3. Zlib
   4. Cygrunsrv
   5. perl
3. Download the OpenSSH Tarball file form www.openssh.org
4. Unpackage the OpenSSH tarball to your /cygwin/usr/local.
5. Download the OpenSSL Fips 140-2 Tarball file from www.openssl.org
6. Unpackage the open OpenSSL  tarball to your /cygwin/usr/local directory
7. Add Cygwin/Bin Directory to Environment Variables
8. Run cygwin
9. Navigate to the Open SSL directory by running
   1. cd usr/local/openSSL
10. Configure the OpenSSL  project
    1. ./configure BSD-generic32  fipscanisterbuild
11. Make the OpenSSL Install
    1. make install
12. Navigate to the Open SSH Directory
    1. cd  /usr
    2. cd /local
    3. cd  /openSSH
13. Configure the OpenSSH project
    1. ./configure –with-ssl-dir=/usr/local/ssl/fips-1.0
14. Register the SSH Service
    1. cygrunsrv --install sshd --path '/usr/local/sbin/sshd' --env 'PATH=/bin;/sbin' --env 'CYGWIN=ntsec tty' -a -D
15. Configure User Accounts
    1. To create a cygwin user create a user in windows then execute mkpasswd –l  >/etc/passwd from the bash command line IIRC.
    2.  mkdir /var/empty
    3.  chown SYSTEM /var/empty
    4.  chmod 755 /var/empty

       755 means read and execute access for everyone and also write access for the owner of the file

    5.  groupadd sshd                
    6.  useradd -g sshd -c 'sshd privsep' -d /var/empty -s /bin/false sshd
16. Make the OpenSSH Install
    1. make install

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