Whenever I need some Cygwin functionality on my Windows hosts, I always prefer pre-packaged solutions (Mobaxterm for ssh client on Windows, CopSSH for SSHD, etc.). This time around I needed a free SSH server for Windows 2012R2 host without the limits imposed by recent CopSSH free version. I decided that I’ll try to use SSHD from cygwin.com directly, something that I tried to avoid in the last decade.

1) INSTALLATION

First you’ll need to download installer from cygwin.com, save the file in some temporary directory. I downloaded 64-bit version because I’ll be installing 64-bit packages. More precisely, I selected the following packages and their dependencies: nano, zip, unzip, OpenSSH, openssl and rlwrap.

Run the installer and follow the wizard, here are screenshots from my host:

2) CONFIGURATION

2.1 Should we edit cygwin.bat?
You’ll probably find numerous recommendation on the net (and even in Oracle documentation — “Enterprise Manager Cloud Control Basic Installation Guide”) that first thing you should do is to open cygwin.bat and insert line set CYGWIN=binmode ntsec, so that bat would look like:

notepad c:\cygwin\cygwin.bat

 
@echo off

C:ssh
chdir C:\cygwin\bin
set CYGWIN=binmode ntsec      << INSERTED LINE
bash --login -i

Both parameters are obsolete in cygwin 1.7, so I believe we can safely skip this step and leave cygwin.bat in original state.

2.2 Test installation
Open C:\cygwin\cygwin.bat and run:

$ cygrunsrv -h

and you should see help for cygwrunsrv, otherwise something went wrong and you’ll likely have to re-install.

2.3 Configure SSHD service by opening cygwin.bat with “Run as Administrator” privilege:

$ ssh-host-config

*** Info: Generating missing SSH host keys
ssh-keygen: generating new host keys: RSA1 RSA DSA ECDSA ED25519
*** Info: Creating default /etc/ssh_config file
*** Info: Creating default /etc/sshd_config file

*** Info: StrictModes is set to 'yes' by default.
*** Info: This is the recommended setting, but it requires that the POSIX
*** Info: permissions of the user's home directory, the user's .ssh
*** Info: directory, and the user's ssh key files are tight so that
*** Info: only the user has write permissions.
*** Info: On the other hand, StrictModes don't work well with default
*** Info: Windows permissions of a home directory mounted with the
*** Info: 'noacl' option, and they don't work at all if the home
*** Info: directory is on a FAT or FAT32 partition.
*** Query: Should StrictModes be used? (yes/no)  yes

*** Info: Privilege separation is set to 'sandbox' by default since
*** Info: OpenSSH 6.1.  This is unsupported by Cygwin and has to be set
*** Info: to 'yes' or 'no'.
*** Info: However, using privilege separation requires a non-privileged account
*** Info: called 'sshd'.
*** Info: For more info on privilege separation read /usr/share/doc/openssh/README.privsep.
*** Query: Should privilege separation be used? (yes/no) yes

*** Info: Note that creating a new user requires that the current account have
*** Info: Administrator privileges.  Should this script attempt to create a
*** Query: new local account 'sshd'? (yes/no) yes

*** Info: Updating /etc/sshd_config file

*** Query: Do you want to install sshd as a service?
*** Query: (Say "no" if it is already installed as a service) (yes/no) yes
*** Query: Enter the value of CYGWIN for the daemon: [] binmode ntsec

*** Info: On Windows Server 2003, Windows Vista, and above, the
*** Info: SYSTEM account cannot setuid to other users -- a capability
*** Info: sshd requires.  You need to have or to create a privileged
*** Info: account.  This script will help you do so.

*** Info: It's not possible to use the LocalSystem account for services
*** Info: that can change the user id without an explicit password
*** Info: (such as passwordless logins [e.g. public key authentication]
*** Info: via sshd) when having to create the user token from scratch.
*** Info: For more information on this requirement, see
*** Info: https://cygwin.com/cygwin-ug-net/ntsec.html#ntsec-nopasswd1

*** Info: If you want to enable that functionality, it's required to create
*** Info: a new account with special privileges (unless such an account
*** Info: already exists). This account is then used to run these special
*** Info: servers.

*** Info: Note that creating a new user requires that the current account
*** Info: have Administrator privileges itself.

*** Info: No privileged account could be found.

*** Info: This script plans to use 'cyg_server'.
*** Info: 'cyg_server' will only be used by registered services.
*** Query: Do you want to use a different name? (yes/no) no
*** Query: Create new privileged user account 'ACMEHOST\cyg_server' (Cygwin name: 'cyg_server')? (yes/no) yes

*** Info: Please enter a password for new user cyg_server.  Please be sure
*** Info: that this password matches the password rules given on your system.
*** Info: Entering no password will exit the configuration.
*** Query: Please enter the password: mysecret
*** Query: Reenter:

*** Info: User 'cyg_server' has been created with password 'mysecret'.
*** Info: If you change the password, please remember also to change the
*** Info: password for the installed services which use (or will soon use)
*** Info: the 'cyg_server' account.

*** Warning: Expected privileged user 'cyg_server' does not exist.
*** Warning: Defaulting to 'SYSTEM'

*** Info: The sshd service has been installed under the LocalSystem
*** Info: account (also known as SYSTEM). To start the service now, call
*** Info: `net start sshd' or `cygrunsrv -S sshd'.  Otherwise, it
*** Info: will start automatically after the next reboot.

*** Info: Host configuration finished. Have fun!

Note the line 33:

*** Query: Enter the value of CYGWIN for the daemon: [] binmode ntsec

Here you should enter any env. variables for cygwin daemon if any. I did NOT set those two variables, they’re here only as a note point. According to cygwin documentation, both parameters are obsolete since Cygwin 1.7, I believe the only reason both parameter are still listed, even in Oracle current documentation, is that someone found some old “how-to” on the net (which was valid before 1.7 release) and took it as granted.

After configuration you should check services, you should see CYGWIN sshd….

and two new local accounts, cyg_server and sshd…

2.4) Enable existing local user account to connect to SSH daemon

// take a backup if by any chance you already have a passwd file (not the case for fresh installation!)

copy C:\cygwin\etc\passwd C:\cygwin\etc\passwd.bak

Open cygwin.bat:

$ /bin/mkpasswd -l -u alesk >> /etc/passwd

The above command will write something like this in the passwd file:

ACMEHOST+alesk:*:197610:197121:U-ACMEHOST\alesk,S-1-5-21-1611771360-925472152-3555864332-1002:/home/alesk:/bin/bash

It means that you can connect to ACMEHOST from some remote workstation with:

$ ssh ACMEHOST+alesk@ACMEHOST

Not cool. I prefer using, simple:

$ ssh alesk@acmehost

so, I changed the username in /etc/passwd to:

alesk:*:197610:197121:U-ACMEHOST\alesk,S-1-5-21-1611771360-925472152-3555864332-1002:/home/alesk:/bin/bash

And for a domain account you would execute:

$ /bin/mkpasswd -d -u alesk >> /etc/passwd
$ mkdir -p /home/alesk
$ chown alesk /home/alesk

2.5) Edit ssh config file:

notepad C:\cygwin\etc\sshd_config

nano /etc/sshd_config

KexAlgorithms diffie-hellman-group-exchange-sha1,diffie-hellman-group1-sha1

2.6 Start SSH daemon:

Cygwin.bat

$ /usr/bin/sshd

or

$ cyrunsrv -S sshd

or start Windows service

Open cmd.exe with “Run as admninistrator”:

cmd> net stop "CYGWIN sshd"

cmd> net start "CYGWIN sshd"

If service doesn’t start check the log at C:\cygwin\var\log\sshd.log.

If you need to add some package afterwards, simply re-run setup.exe installer and check additional packages that you want to install.