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Manually install OpenSSH in Windows Server

How to install OpenSSH Server in Windows Server 2019 Core using PowerShell, or Windows Server 2016

OpenSSH is an ideal and secure way of performing remote maintenance & administration on your servers. Even on Windows Server! :) Microsoft have released their OpenSSH port for Windows Server and Windows 10 back in 2015. Here is how to install the OpenSSH Server on Windows Server 2016 and 2019.

In this small tutorial, I’m not using PowerShell’s Add-WindowsCapability cmdlet, because it errors out on unsupported platforms. And I want to be able to customize the sshd installation directory. If you follow this post, you can install Microsoft OpenSSH Server on Windows Server 2016 and even Windows Server 2012 R2, in a folder of your choosing.

Prerequisites

In order to be able to install OpenSSH on Windows, you need the software. Doh! :-)

  1. Download the latest release from GitHub: https://github.com/PowerShell/Win32-OpenSSH/releases (OpenSSH-Win64.zip for example).

Install “Windows for OpenSSH” using PowerShell

  1. Unblock the downloaded OpenSSH archive if necessary: Unblock-File .\Downloads\OpenSSH-Win64.zip
  2. Extract the archive: Expand-Archive .\Downloads\OpenSSH-Win64.zip -DestinationPath .
  3. Copy the OpenSSH-Win64 folder to your desired location, e.g c: Copy-Item -Recurse .\OpenSSH-Win64\ 'C:\'
  4. The libcrypto.dll file has to be accessible for all users: &icacls C:\OpenSSH-Win64\libcrypto.dll /grant Everyone:RX
  5. Run install-sshd.ps1 to create the OpenSSH Authentication Agent and OpenSSH SSH Server services. It also sets some permissions and registers an Event Tracing (ETW) provider.
  6. Change the service startup to Automatic. The OpenSSH SSH Server service is set to Manual startup, not automatic: &sc.exe config sshd start= auto, &sc.exe config ssh-agent start= auto
  7. Start the OpenSSH Authentication Agent and SSH Server services: &sc.exe start sshd, &sc.exe start ssh-agent
  8. Make sure your Windows Defender Firewall is open for port 22, rule OpenSSH-Server-In-TCP must be enabled. If this rule is not available, manually create it:
New-NetFirewallRule -Name sshd -DisplayName 'OpenSSH SSH Server' -Enabled True -Direction Inbound -Protocol TCP -Action Allow -LocalPort 22 -Program "C:\Windows\System32\OpenSSH\sshd.exe"

Replace C:\Windows\System32\OpenSSH\sshd.exe with the actual path to the sshd.exe (C:\OpenSSH\sshd.exe, if you followed this instruction). Or go to Control Panel > System and Security > Windows Firewall1 > Advanced Settings > Inbound Rules and add a new rule for port 22.

Let’s connect!

PS C:\> ssh -l janreilink localhost
Connect to local OpenSSH server in Windows
Connect to local OpenSSH server in Windows

sshd_config

Often you not only need to install OpenSSH, you also need to configure it. For this, OpenSSH on Windows uses an mechanism where the default sshd_config (called “sshd_config_default”) is located in the directory to where you’ve unpacked the OpenSSH-Win64.zip archive. When you start the service, the file is copied to C:\ProgramData\ssh\sshd_config.

In Windows, sshd reads configuration data from %programdata%\ssh\sshd_config by default, or a different configuration file may be specified by launching sshd.exe with the -f parameter. If the file is absent, sshd generates one with the default configuration when the service is started.

https://docs.microsoft.com/en-us/windows-server/administration/openssh/openssh_server_configuration#windows-configurations-in-sshd_config

So you can either make you configuration in the sshd_config_default file, that is copied when you start the service for the first time, or you start and stop OpenSSH, edit C:\ProgramData\ssh\sshd_config and restart OpenSSH again.

Older Windows Server versions

OpenSSH Server on Windows Server 2012 R2, you said? Yes, you can use the same method to setup OpenSSH in Windows Server 2012 R2 (version 6.3.9600).

Here is a screenshot of connecting to sshd on Windows version 6.3.9600:

Connect to local OpenSSH server in Windows Server 2012 R2

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