{"id":7978,"date":"2020-12-17T15:43:58","date_gmt":"2020-12-17T20:43:58","guid":{"rendered":"https:\/\/jdhitsolutions.com\/blog\/?p=7978"},"modified":"2020-12-17T15:44:08","modified_gmt":"2020-12-17T20:44:08","slug":"deploy-openssh-to-windows-server","status":"publish","type":"post","link":"https:\/\/jdhitsolutions.com\/blog\/powershell\/7978\/deploy-openssh-to-windows-server\/","title":{"rendered":"Deploy OpenSSH to Windows Server"},"content":{"rendered":"\n

Yesterday I shared some PowerShell ideas for remotely setting up the server component of ssh<\/em><\/a> <\/em>on a remote Windows 10 system. This would allow you to establish an ssh session to the desktop or even use PowerShell remoting over ssh. Next, we need to look at doing the same thing for Windows Servers.<\/p>\n\n\n\n

Windows Server 2019<\/h2>\n\n\n\n

If you are using Windows Server 2019, you can use the same code I used with Windows 10, at least based on my experiences. Windows Server 2019 includes the OpenSSH.Server capability that you can install with Add-WindowsCapability. I was able to use the same deployment script I used with Windows 10 to install PowerShell 7 and sshd. The only change I made was to the Write-Progress activity.<\/p>\n\n\n\n

$prog\u00a0=\u00a0@{\n\u00a0\u00a0\u00a0\u00a0Activity\u00a0=\u00a0\"Deploy\u00a0SSH\u00a0Server\u00a0to\u00a0Windows\u00a010\/Windows\u00a0Server\u00a02019\"\n\u00a0\u00a0\u00a0\u00a0Status\u00a0=\u00a0$Computername.toUpper()\n\u00a0\u00a0\u00a0\u00a0CurrentOperation\u00a0=\u00a0\"\"\n\u00a0\u00a0\u00a0\u00a0PercentComplete\u00a0=\u00a00\n}<\/code><\/pre>\n\n\n\n
Otherwise, everything ran the same and in minutes PowerShell 7 and ssh remoting were ready to go.<\/p>\n\n\n\n
\"Windows<\/a><\/figure>\n\n\n\n
Windows Server 2016<\/h2>\n\n\n\n
Installing for Windows Server 2016 is a bit different. According to the Microsoft documentation that I could find, you need to install the latest bits from GitHub. You can do that with Invoke-Webrequest. Although before you do anything, you will most likely need to configure network security.<\/p>\n\n\n\n
[Net.ServicePointManager]::SecurityProtocol\u00a0=\u00a0[Net.SecurityProtocolType]::Tls12<\/code><\/pre>\n\n\n\n
If you don't do this on Windows Server 2016, you'll get errors trying to connect to GitHub and the PowerShell Gallery. Once the zip file is downloaded, you can extract it and then run the setup script. Here's the server-focused PowerShell script.<\/p>\n\n\n\n
#requires\u00a0-version\u00a05.1<\/em>\n\n<#<\/em>\n\u00a0\u00a0\u00a0\u00a0setup\u00a0SSHD\u00a0on\u00a0Windows\u00a0Server\u00a02016<\/em>\n\u00a0\u00a0\u00a0\u00a0https:\/\/github.com\/PowerShell\/Win32-OpenSSH\/wiki\/Install-Win32-OpenSSH<\/em>\n\n\u00a0\u00a0\u00a0\u00a0This\u00a0script\u00a0is\u00a0designed\u00a0to\u00a0be\u00a0run\u00a0remotely\u00a0using\u00a0Invoke-Command<\/em>\n\n\u00a0\u00a0\u00a0\u00a0Sample\u00a0usage:<\/em>\n\u00a0\u00a0\u00a0\u00a0Verbose\u00a0and\u00a0Whatif<\/em>\n\u00a0\u00a0\u00a0\u00a0invoke-command\u00a0-FilePath\u00a0.\\Setup-SSHServer2.ps1\u00a0-ComputerName\u00a0srv1\u00a0-cred\u00a0$admin\u00a0-ArgumentList\u00a0@(\"Continue\",$True)<\/em>\n\n\u00a0\u00a0\u00a0\u00a0Verbose<\/em>\n\u00a0\u00a0\u00a0\u00a0invoke-command\u00a0-FilePath\u00a0.\\Setup-SSHServer2.ps1\u00a0-ComputerName\u00a0srv1\u00a0-cred\u00a0$admin\u00a0-ArgumentList\u00a0@(\"Continue\")<\/em>\n#><\/em>\n\n[cmdletbinding(SupportsShouldProcess<\/em>)]\nParam([string]$VerboseOption\u00a0=\u00a0\"SilentlyContinue\",\u00a0[bool]$WhatIfOption\u00a0=\u00a0$False)\n\n$VerbosePreference\u00a0=\u00a0$VerboseOption\n$WhatIfPreference\u00a0=\u00a0$WhatIfOption\n\n[Net.ServicePointManager]::SecurityProtocol\u00a0=\u00a0[Net.SecurityProtocolType]::Tls12\n$url\u00a0=\u00a0'https:\/\/github.com\/PowerShell\/Win32-OpenSSH\/releases\/latest\/'\n$request\u00a0=\u00a0[System.Net.WebRequest]::Create($url)\n$request.AllowAutoRedirect\u00a0=\u00a0$false\n$response\u00a0=\u00a0$request.GetResponse()\n$dl\u00a0=\u00a0$([String]$response.GetResponseHeader(\"Location\")).Replace('tag',\u00a0'download')\u00a0+\u00a0'\/OpenSSH-Win64.zip'\n\n$zip\u00a0=\u00a0\"C:\\OpenSSH64.zip\"\nWrite-Verbose\u00a0\"download\u00a0SSH\u00a0from\u00a0$dl\u00a0to\u00a0$zip\"\nif\u00a0($pscmdlet.ShouldProcess($dl,\"Downloading\u00a0OpenSSH-Win64\u00a0Package\"))\u00a0{\n\u00a0\u00a0\u00a0\u00a0Try\u00a0{\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Invoke-WebRequest\u00a0-Uri\u00a0$dl\u00a0-OutFile\u00a0$zip\u00a0-DisableKeepAlive\u00a0-ErrorAction\u00a0Stop\n\u00a0\u00a0\u00a0\u00a0}\n\u00a0\u00a0\u00a0\u00a0Catch\u00a0{\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Throw\u00a0$_\n\u00a0\u00a0\u00a0\u00a0}\n\u00a0\u00a0\u00a0\u00a0if\u00a0(Test-Path\u00a0$zip)\u00a0{\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Write-Verbose\u00a0\"Extract\u00a0zip\u00a0file\"\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Expand-Archive\u00a0$zip\u00a0-DestinationPath\u00a0\"c:\\Program\u00a0Files\"\u00a0-force\n\u00a0\u00a0\u00a0\u00a0}\n\u00a0\u00a0\u00a0\u00a0else\u00a0{\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Return\u00a0\"zip\u00a0file\u00a0failed\u00a0to\u00a0download\"\n\u00a0\u00a0\u00a0\u00a0}\n}\n\nWrite-Verbose\u00a0\"Install\u00a0SSH\"\nif\u00a0($pscmdlet.ShouldProcess(\"install-sshd.ps1\",\u00a0\"Execute\"))\u00a0{\n\u00a0\u00a0\u00a0\u00a0Push-Location\n\u00a0\u00a0\u00a0\u00a0Set-Location\u00a0-Path\u00a0'C:\\Program\u00a0Files\\OpenSSH-Win64\\'\n\u00a0\u00a0\u00a0\u00a0.\u00a0.\\install-sshd\n\u00a0\u00a0\u00a0\u00a0Pop-Location\n}\n\nWrite-Verbose\u00a0\"Set\u00a0sshd\u00a0to\u00a0auto\u00a0start\"\nTry\u00a0{\n\u00a0\u00a0\u00a0\u00a0if\u00a0($pscmdlet.ShouldProcess(\"sshd\",\u00a0\"Configure\u00a0service\"))\u00a0{\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Set-Service\u00a0-Name\u00a0sshd\u00a0-StartupType\u00a0Automatic\u00a0-ErrorAction\u00a0stop\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Write-Verbose\u00a0\"Start\u00a0the\u00a0sshd\u00a0service\"\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Start-Service\u00a0-Name\u00a0sshd\u00a0-ErrorAction\u00a0Stop\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Get-Service\u00a0sshd\u00a0|\u00a0Select-Object\u00a0-Property\u00a0*\u00a0|\u00a0Out-String\u00a0|\u00a0Write-Verbose\n\u00a0\u00a0\u00a0\u00a0}\n}\nCatch\u00a0{\n\u00a0\u00a0\u00a0\u00a0Write-Warning\u00a0\"There\u00a0was\u00a0a\u00a0problem\u00a0configuring\u00a0the\u00a0sshd\u00a0service.\"\n}\n\nWrite-Verbose\u00a0\"Add\u00a0the\u00a0firewall\u00a0rule\"\nif\u00a0($pscmdlet.ShouldProcess(\"sshd\",\u00a0\"Add\u00a0firewall\u00a0rule\"))\u00a0{\n\u00a0\u00a0\u00a0\u00a0Try\u00a0{\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0$rule\u00a0=\u00a0New-NetFirewallRule\u00a0-Name\u00a0sshd\u00a0-DisplayName\u00a0'OpenSSH\u00a0Server\u00a0(sshd)'\u00a0-Enabled\u00a0True\u00a0-Direction\u00a0Inbound\u00a0-Protocol\u00a0TCP\u00a0-Action\u00a0Allow\u00a0-LocalPort\u00a022\u00a0-ErrorAction\u00a0Stop\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Write-Verbose\u00a0($rule\u00a0|\u00a0Out-String)\n\u00a0\u00a0\u00a0\u00a0}\n\u00a0\u00a0\u00a0\u00a0Catch\u00a0{\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Throw\u00a0$_\n\u00a0\u00a0\u00a0\u00a0}\n}\n\nif\u00a0(-Not\u00a0$WhatIfOption)\u00a0{\n\u00a0\u00a0\u00a0\u00a0#only\u00a0display\u00a0the\u00a0summary\u00a0if\u00a0not\u00a0using\u00a0-WhatIf<\/em>\n\u00a0\u00a0\u00a0\u00a0$msg\u00a0=\u00a0@\"\n\nSSH\u00a0setup\u00a0complete.\u00a0Edit\u00a0$ENV:ProgramData\\ssh\\sshd_config\u00a0for\u00a0additional\u00a0configurations\u00a0options\nor\u00a0to\u00a0enable\u00a0remoting\u00a0under\u00a0PowerShell\u00a07.\n\nYou\u00a0will\u00a0need\u00a0to\u00a0restart\u00a0the\u00a0sshd\u00a0service\u00a0for\u00a0changes\u00a0to\u00a0take\u00a0effect.\n\n\"@\n\u00a0\u00a0\u00a0\u00a0Write-Host\u00a0$msg\u00a0-ForegroundColor\u00a0green\n}\n\nWrite-Verbose\u00a0\"Ending\u00a0SSHD\u00a0setup\u00a0process.\"<\/code><\/pre>\n\n\n\n
As with the Windows 10 version of the script, this is designed to be run remotely using Invoke-Command.  And of course, I have a control script.<\/p>\n\n\n\n
#requires\u00a0-version\u00a05.1<\/em>\n\n#Deployment\u00a0control\u00a0script\u00a0to\u00a0setup\u00a0SSH\u00a0server\u00a0on\u00a0a\u00a0remote\u00a0Windows\u00a0Server\u00a02016<\/em>\n#It\u00a0is\u00a0assumed\u00a0PowerShell\u00a07\u00a0is,\u00a0or\u00a0will\u00a0be,\u00a0installed.<\/em>\n\n[cmdletbinding(SupportsShouldProcess<\/em>)]\nParam(\n\u00a0\u00a0\u00a0\u00a0[Parameter(Position<\/em>\u00a0=\u00a00,\u00a0Mandatory<\/em>)]\n\u00a0\u00a0\u00a0\u00a0[string]$Computername,\n\u00a0\u00a0\u00a0\u00a0[pscredential]$Credential,\n\u00a0\u00a0\u00a0\u00a0[switch]$InstallPowerShell\n)\n\n#remove\u00a0parameters\u00a0from\u00a0PSBoundparameter\u00a0that\u00a0don't\u00a0apply\u00a0to\u00a0New-PSSession<\/em>\nif\u00a0($PSBoundParameters.ContainsKey(\"InstallPowerShell\"))\u00a0{\n\u00a0\u00a0\u00a0\u00a0[void]($PSBoundParameters.remove(\"InstallPowerShell\"))\n}\n\nif\u00a0($PSBoundParameters.ContainsKey(\"WhatIf\"))\u00a0{\n\u00a0\u00a0\u00a0\u00a0[void]($PSBoundParameters.remove(\"WhatIf\"))\n}\n\n#parameters\u00a0for\u00a0Write-Progress<\/em>\n$prog\u00a0=\u00a0@{\n\u00a0\u00a0\u00a0\u00a0Activity\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0=\u00a0\"Deploy\u00a0SSH\u00a0Server\u00a0to\u00a0Windows\u00a0Server\u00a02016\"\n\u00a0\u00a0\u00a0\u00a0Status\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0=\u00a0$Computername.toUpper()\n\u00a0\u00a0\u00a0\u00a0CurrentOperation\u00a0=\u00a0\"\"\n\u00a0\u00a0\u00a0\u00a0PercentComplete\u00a0\u00a0=\u00a00\n}\n#create\u00a0the\u00a0PSSession<\/em>\nTry\u00a0{\n\u00a0\u00a0\u00a0\u00a0Write-Verbose\u00a0\"Creating\u00a0a\u00a0PSSession\u00a0to\u00a0$Computername\"\n\u00a0\u00a0\u00a0\u00a0$prog.CurrentOperation\u00a0=\u00a0\"Creating\u00a0a\u00a0temporary\u00a0PSSession\"\n\u00a0\u00a0\u00a0\u00a0$prog.PercentComplete\u00a0=\u00a010\n\u00a0\u00a0\u00a0\u00a0Write-Progress\u00a0@prog\n\u00a0\u00a0\u00a0\u00a0$sess\u00a0=\u00a0New-PSSession\u00a0@PSBoundParameters\u00a0-ErrorAction\u00a0Stop\n}\nCatch\u00a0{\n\u00a0\u00a0\u00a0\u00a0Throw\u00a0$_\n}\n\nif\u00a0($sess)\u00a0{\n\u00a0\u00a0\u00a0\u00a0if\u00a0($InstallPowerShell)\u00a0{\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Write-Verbose\u00a0\"Installing\u00a0PowerShell\u00a07\"\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0$prog.currentOperation\u00a0=\u00a0\"Installing\u00a0PowerShell\u00a07\"\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0$prog.percentComplete\u00a0=\u00a025\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Write-Progress\u00a0@prog\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0#install\u00a0PowerShell<\/em>\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0if\u00a0($pscmdlet.ShouldProcess($Computername.toUpper(),\u00a0\"Install\u00a0PowerShell\u00a07\"))\u00a0{\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Invoke-Command\u00a0-ScriptBlock\u00a0{\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0#need\u00a0to\u00a0set\u00a0security\u00a0protocol\u00a0to\u00a0Tls12\u00a0for\u00a0Windows\u00a0Server\u00a02016\u00a0otherwise\u00a0the\u00a0installs\u00a0will\u00a0fail<\/em>\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Write-Verbose\u00a0\"Setting\u00a0network\u00a0security\u00a0to\u00a0Tls12\"\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0[Net.ServicePointManager]::SecurityProtocol\u00a0=\u00a0[Net.SecurityProtocolType]::Tls12\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Write-Verbose\u00a0\"Using\u00a0Security\u00a0Protocol\u00a0$([Net.ServicePointManager]::SecurityProtocol)\"\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0[void](Install-PackageProvider\u00a0-Name\u00a0nuget\u00a0-force\u00a0-forcebootstrap\u00a0-minimumversion\u00a0'2.8.5.201')\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Install-Module\u00a0PSReleaseTools\u00a0-Force\u00a0-Scope\u00a0AllUsers\u00a0-Repository\u00a0PSGallery\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Install-PowerShell\u00a0-EnableRemoting\u00a0-EnableContextMenu\u00a0-Mode\u00a0Quiet\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0}\u00a0-Session\u00a0$sess\n\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0#Installing\u00a0PowerShell\u00a0may\u00a0break\u00a0the\u00a0session\u00a0so\u00a0rebuild\u00a0it\u00a0if\u00a0necessary<\/em>\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0if\u00a0($sess.state\u00a0-eq\u00a0'Broken')\u00a0{\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0Write-Verbose\u00a0\"Rebuilding\u00a0the\u00a0temporary\u00a0PSSession\"\n\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u0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The script supports -Verbose and -WhatIf.<\/p>\n\n\n\n
\"\"<\/a><\/figure>\n\n\n\n
The script will copy the sshd_config_default file which you can grab from the previous post. Once in place, remoting with ssh in PowerShell 7 is a breeze.<\/p>\n\n\n\n
\"\"<\/a><\/figure>\n\n\n\n
Next Steps<\/h2>\n\n\n\n
You should test all of this code in a non-production environment and adjust as necessary. Anytime you play with remoting, you run the risk of leaving yourself vulnerable. Part of this process should include learning more about ssh. All I've done is get it installed and able to work with PowerShell. There is much more to ssh<\/p>\n\n\n\n
Comments and questions welcome.<\/p>\n","protected":false},"excerpt":{"rendered":"
Yesterday I shared some PowerShell ideas for remotely setting up the server component of ssh on a remote Windows 10 system. This would allow you to establish an ssh session to the desktop or even use PowerShell remoting over ssh. Next, we need to look at doing the same thing for Windows Servers. Windows Server…<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_monsterinsights_skip_tracking":false,"_monsterinsights_sitenote_active":false,"_monsterinsights_sitenote_note":"","_monsterinsights_sitenote_category":0,"_jetpack_memberships_contains_paid_content":false,"footnotes":"","jetpack_publicize_message":"new on the blog: Deploy OpenSSH to Windows Server #PowerShell #PS7Now","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","default_image_id":0,"font":"","enabled":false},"version":2}},"categories":[4,610,8],"tags":[624,613],"class_list":["post-7978","post","type-post","status-publish","format-standard","hentry","category-powershell","category-powershell-7","category-scripting","tag-ps7now","tag-ssh"],"yoast_head":"\nDeploy OpenSSH to Windows Server • The Lonely 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