Installing an SSH Server on Windows 2003

This series of articles will show how to install SSHd ( OpenSSH) by using Cygwin. One benefit of using Cygwin for this is that we get the result:

[usr-1@srv-1 ~]$ ssh administrator@ 'cat /proc/meminfo'
total:      used:      free:
Mem:   964116480  231288832  732827648
Swap: 1447034880    8290304 1438744576
MemTotal:         941520 kB
MemFree:          715652 kB
MemShared:             0 kB
HighTotal:             0 kB
HighFree:              0 kB
LowTotal:         941520 kB
LowFree:          715652 kB
SwapTotal:       1413120 kB
SwapFree:        1405024 kB
[usr-1@srv-1 ~]$

What just happened? We returned the memory statistics of a Windows 2003 server in GNU/Linux /proc/meminfo format. Note that this series is specific to Windows Server 2003. There are minor differences with Windows 2000 and XP. This will also work on NT with more changes. For an excellent document that is more general and complete, see How to install OpenSSH sshd server and sftp server on a Windows 2000 or Windows XP or Windows Server 2003 by Nicholas Fong.

OK. Let's install this puppy.

Grab setup.exe from the Cygwin website, copy it to a folder on a drive with room to grow, and run it:


We are using version 2.510.2.2. Click Next to continue:


Choose Install from Internet and click Next to continue:


Make sure the root directory is what you want, and click Next to continue:


Choose a different path for the packages, since you may want to delete them when you are done to save space:

Select your Internet connection type:


Choose the closest, most available download site:


When the packages are finished downloading, you will see a screen like this:


Scroll down, expand the net section, and put an x through the binary box of openssh and rsync by clicking on the Skip cycle arrows. This will also automatically install dependencies:


Expand the edit section, and put an x through vim:


A progress page will show the packages as they are downloaded and installed:


Choose where you want icons:


Start cygwin by double clicking on the icons (wherever). Some initial configuration will take place automatically:

Copying skeleton files.
These files are for the user to personalise
their cygwin experience.
These will never be overwritten.
`./.bashrc' -> `/home/Administrator//.bashrc'
`./.bash_profile' -> `/home/Administrator//.bash_profile'
`./.inputrc' -> `/home/Administrator//.inputrc'
Administrator@win1 ~

Run the ssh-host-config script, and answer the questions:

$ ssh-host-config
Generating /etc/ssh_host_key
Generating /etc/ssh_host_rsa_key
Generating /etc/ssh_host_dsa_key
Generating /etc/ssh_config file
Privilege separation is set to yes by default since OpenSSH 3.3.
However, this requires a non-privileged account called 'sshd'.
For more info on privilege separation read /usr/share/doc/openssh/README.privsep.
Should privilege separation be used? (yes/no) yes
Warning: The following function requires administrator privileges!
Should this script create a local user 'sshd' on this machine? (yes/no) yes
Generating /etc/sshd_config file
Added ssh to C:\WINDOWS\system32\drivers\etc\services
Warning: The following functions require administrator privileges!
Do you want to install sshd as service?
(Say "no" if it's already installed as service) (yes/no) yes
You appear to be running Windows 2003 Server or later.  On 2003 and
later systems, it's not possible to use the LocalSystem account
if sshd should allow passwordless logon (e. g. public key authentication).
If you want to enable that functionality, it's required to create a new
account 'sshd_server' with special privileges, which is then used to run
the sshd service under.
Should this script create a new local account 'sshd_server' which has
the required privileges? (yes/no) yes
Please enter a password for new user 'sshd_server'.  Please be sure that
this password matches the password rules given on your system.
Entering no password will exit the configuration.  PASSWORD=password
User 'sshd_server' has been created with password 'password'.
If you change the password, please keep in mind to change the password
for the sshd service, too.
Also keep in mind that the user sshd_server needs read permissions on all
users' .ssh/authorized_keys file to allow public key authentication for
these users!.  (Re-)running ssh-user-config for each user will set the
required permissions correctly.
Which value should the environment variable CYGWIN have when
sshd starts? It's recommended to set at least "ntsec" to be
able to change user context without password.
Default is "ntsec".  CYGWIN=ntsec
The service has been installed under sshd_server account.
To start the service, call `net start sshd' or `cygrunsrv -S sshd'.
Host configuration finished. Have fun!
Administrator@win1 ~

Start the service:

$ net start sshd
The CYGWIN sshd service is starting.
The CYGWIN sshd service was started successfully.
Administrator@win1 ~

Here is the Windows service information:


Test out SSH:

[usr-1@srv-1 ~]$ ssh administrator@
The authenticity of host ' (' can't be established.
RSA key fingerprint is 28:d1:72:f3:02:fa:46:ba:80:3a:61:86:18:6a:3b:4d.
Are you sure you want to continue connecting (yes/no)? yes
Warning: Permanently added '' (RSA) to the list of known hosts.
administrator@'s password:
Administrator@win1 ~

If you would like to copy your public key over to the server, make a directory for it on the Windows box with SSHd:

$ mkdir ~/.ssh

If you don't have a public key, that is beyond the scope of this article. A hint is that you need to use ssh-keygen -t dsa; however, there are implications to this and better ways to do it in some cases. Let's assume you have an key, copy it over, and log on, this time without having to enter a password:

[usr-1@srv-1 ~]$ scp ~/.ssh/ administrator@
administrator@'s password:                                    100%  621     0.6KB/s   00:00
[usr-1@srv-1 ~]$ ssh administrator@ 
Last login: Fri Mar 
17 14:47:04 2006 from sv-1 
Administrator@win1 ~

We can now run some simple remote commands to get CPU and memory info from the Windows server:

[usr-1@srv-1 ~]$ ssh administrator@ 'cat /proc/meminfo'
total:      used:      free:
Mem:   964116480  231288832  732827648
Swap: 1447034880    8290304 1438744576
MemTotal:         941520 kB
MemFree:          715652 kB
MemShared:             0 kB
HighTotal:             0 kB
HighFree:              0 kB
LowTotal:         941520 kB
LowFree:          715652 kB
SwapTotal:       1413120 kB
SwapFree:        1405024 kB
[usr-1@srv-1 ~]$ ssh administrator@ 'cat /proc/cpuinfo'
processor       : 0
vendor_id       : GenuineIntel
type            : primary processor
cpu family      : 15
model           : 1
model name      : Intel(R) Pentium(R) 4 CPU 1.70GHz
stepping        : 2
brand id        : 8
cpu count       : 1
apic id         : 0
cpu MHz         : 1715
fpu             : yes
flags           : fpu vme de pse tsc msr pae mce cx8 apic sep mtrr pge 
mca cmov pat pse36 clfl dtes acpi mmx fxsr sse sse2 ss htt tmi
[usr-1@srv-1 ~]$


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