Is it possible to update the built-in OpenSSH Client in Windows 10?

Question

I'm experiencing certain issues with the built-in OpenSSH client that, according to the Win32-OpenSSH Github page, seem resolved in newer versions. The newest version is v7.9 while the preinstalled client is in version 7.6p1.

PS C:\> ssh -V
OpenSSH_for_Windows_7.6p1, LibreSSL 2.6.4

I understand it's possible to install OpenSSH both as an optional feature in the "apps & features" settings page, or using Powershell. That seems futile in my situation as the client clearly already is installed.

PS C:\>  Get-WindowsCapability -Online | ? Name -like 'OpenSSH*'

Name  : OpenSSH.Client~~~~0.0.1.0
State : Installed

Name  : OpenSSH.Server~~~~0.0.1.0
State : NotPresent

Unfortunately, it doesn't seem possible to update the client this way and the Github page doesn't seem to publish binaries. Does this mean I have to make the binaries myself if I want to use newer versions, and would they even work as a replacement not being signed or anything? Is there maybe a simpler way?

Answer 1

This page gives the steps to follow using Powershell to install the latest packages.

[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12
$url = 'https://github.com/PowerShell/Win32-OpenSSH/releases/latest/'
$request = [System.Net.WebRequest]::Create($url)
$request.AllowAutoRedirect=$false
$response=$request.GetResponse()
$([String]$response.GetResponseHeader("Location")).Replace('tag','download') + '/OpenSSH-Win64.zip'  
$([String]$response.GetResponseHeader("Location")).Replace('tag','download') + '/OpenSSH-Win32.zip'

If you use Chocolatey, then type the following in the command prompt as shown here:

choco upgrade openssh

Answer 2

The answer to overwrite the files works:

Download the latest and update them in C:\Windows\System32.

However, this is easier said than done due to how Windows restricts permissions to modify/write files in System32. Running PowerShell as Administrator was not sufficient to modify files. I had to change ownership and add full control permissions to get it done as follows:

# Download upstream bins
$url = 'https://github.com/PowerShell/Win32-OpenSSH/releases/latest/'
$request = [System.Net.WebRequest]::Create($url)
$request.AllowAutoRedirect=$false
$response=$request.GetResponse()
$source = $([String]$response.GetResponseHeader("Location")).Replace('tag','download') + '/OpenSSH-Win64.zip'
(New-Object System.Net.WebClient).DownloadFile($source, 'OpenSSH-Win64.zip')



# Overwrite windows installed bins
$openSshBins = (Get-ChildItem 'C:\WINDOWS\System32\OpenSSH\').Name
Expand-Archive -Path .\OpenSSH-Win64.zip -DestinationPath .
takeown.exe /a /r /f C:\Windows\System32\OpenSSH\
icacls.exe 'C:\Windows\System32\OpenSSH' /grant 'BUILTIN\Administrators:(OI)(CI)F'
icacls.exe 'C:\Windows\System32\OpenSSH' /grant 'BUILTIN\Administrators:F' /t
Stop-Service ssh-agent
$openSshBins | %{ Copy-Item -Path .\OpenSSH-Win64\$_ -Destination C:\Windows\System32\OpenSSH\ }
Start-Service ssh-agent

Note, to auotmate the download, you need to permit redirects.

Answer 3

The binaries are now on GitHub. Download the latest and update them in C:\Windows\System32.

Answer 4

1. Remove the default version of OpenSSH:

Remove-WindowsCapability -Online -Name OpenSSH.Client~~~~0.0.1.0

2. Install the recent version:

• using Windows Package Manager:

  winget install openssh
  

• manually from GitHub (see Install Win32 OpenSSH Using MSI)

3. Add it to path:

[Environment]::SetEnvironmentVariable("Path", 
$env:Path + ';' + ${Env:ProgramFiles} + '\OpenSSH', 
[System.EnvironmentVariableTarget]::Machine)