diff --git a/sshd/README.md b/sshd/README.md
new file mode 100644
index 000000000..2af1e1ddb
--- /dev/null
+++ b/sshd/README.md
@@ -0,0 +1,30 @@
+---
+title: OpenSSH (for Windows)
+homepage: https://webinstall.dev/sshd
+tagline: |
+  OpenSSH: Window's built-in SSH implementation for remote login
+---
+
+To update (replacing the current version) run `webi sudo`.
+
+## Cheat Sheet
+
+> Does the tedious work of installing, registering, and starting Windows' built-in  OpenSSH Server (`sshd`)
+
+As this requires Administrator permissions, you must run the command yourself:
+
+```sh
+sshd-service-install
+```
+
+### Files
+
+These are the files / directories that are created and/or modified with this
+install:
+
+```text
+~/.local/bin/sudo.bat
+~/.local/bin/sshd-service-install.bat
+```
+
+
diff --git a/sshd/install.ps1 b/sshd/install.ps1
new file mode 100644
index 000000000..fd96fae1c
--- /dev/null
+++ b/sshd/install.ps1
@@ -0,0 +1,52 @@
+#!/usr/bin/env pwsh
+
+$ErrorActionPreference = 'stop'
+
+function Repair-MissingCommand {
+    Param(
+        [string]$Name,
+        [string]$Package,
+        [string]$Command
+    )
+
+    Write-Host "    Checking for $Name ..."
+    $HasCommand = Get-Command -Name $Command -ErrorAction Silent
+    IF ($HasCommand) {
+        Return
+    }
+
+    & $HOME\.local\bin\webi-pwsh.ps1 $Package
+    $null = Sync-EnvPath
+}
+
+function Install-WebiHostedScript () {
+    Param(
+        [string]$Package,
+        [string]$ScriptName
+    )
+    $PwshName = "_${ScriptName}.ps1"
+    $PwshUrl = "${Env:WEBI_HOST}/packages/${Package}/${ScriptName}.ps1"
+    $PwshPath = "$HOME\.local\bin\${PwshName}"
+    $OldPath = "$HOME\.local\bin\${ScriptName}.ps1"
+
+    $BatPath = "$HOME\.local\bin\${ScriptName}.bat"
+    $PwshExec = "powershell -ExecutionPolicy Bypass"
+    $Bat = "@echo off`r`n$PwshExec %USERPROFILE%\.local\bin\${PwshName} %*"
+
+    Invoke-DownloadUrl -Force -URL $PwshUrl -Path $PwshPath
+    Set-Content -Path $BatPath -Value $Bat
+    Write-Host "    Created alias ${BatPath}"
+    Write-Host "      to run ${PwshPath}"
+
+    # fix for old installs
+    Remove-Item -Path $OldPath -Force -ErrorAction Ignore
+}
+
+
+Repair-MissingCommand -Name "sudo (RunAs alias)" -Package "sudo" -Command "sudo"
+Install-WebiHostedScript -Package "sshd" -ScriptName "sshd-service-install"
+
+Write-Output ""
+Write-Output "${TTask}Copy, paste, and run${TReset} the following to install sshd as a system service"
+Write-Output "    ${TCmd}sshd-service-install${TReset}"
+Write-Output ""
diff --git a/sshd/install.sh b/sshd/install.sh
new file mode 100644
index 000000000..7c4262cd2
--- /dev/null
+++ b/sshd/install.sh
@@ -0,0 +1,35 @@
+__install_sshd() {
+    my_os="$(uname -s)"
+    if test "Darwin" = "${my_os}"; then
+        echo >&2 ""
+        echo >&2 "Copy, paste, and run the following to enable the built-in sshd:"
+        echo >&2 "    sudo systemsetup -f -setremotelogin on"
+        echo >&2 "    sudo systemsetup -getremotelogin"
+        echo >&2 ""
+        exit 1
+    fi
+
+    echo >&2 "Install and enable sshd using your system package manager:"
+    my_cmd=""
+    if test command -v sudo > /dev/null; then
+        my_cmd="sudo "
+    fi
+
+    if test command -v apt > /dev/null; then
+        echo "    ${my_cmd}apt install -y openssh-server"
+        echo "    ${my_cmd}systemctl enable ssh"
+        echo "    ${my_cmd}systemctl start ssh"
+    elif test command -v yum > /dev/null; then
+        echo "    ${my_cmd}yum -y install openssh-server"
+        echo "    ${my_cmd}systemctl enable ssh"
+        echo "    ${my_cmd}systemctl start ssh"
+    elif test command -v apk > /dev/null; then
+        echo "    ${my_cmd}apk add --no-cache openssh"
+        echo "    ${my_cmd}service sshd added to runlevel default"
+        echo "    ${my_cmd}service sshd start"
+    else
+        echo "    (unknown package manager / init daemon)"
+    fi
+
+    exit 1
+}
diff --git a/sshd/sshd-service-install.ps1 b/sshd/sshd-service-install.ps1
new file mode 100644
index 000000000..d2ceeadc6
--- /dev/null
+++ b/sshd/sshd-service-install.ps1
@@ -0,0 +1,62 @@
+#!/usr/bin/env pwsh
+
+$Esc = [char]27
+$Warn = "${Esc}[1m[33m"
+$ResetAll = "${Esc}[0m"
+
+# See
+#   - <https://gist.github.com/HacDan/026fa8d7d4130fbbc2409d84c2d04143#load-public-keys>
+#   - <https://techcommunity.microsoft.com/t5/itops-talk-blog/installing-and-configuring-openssh-on-windows-server-2019/ba-p/309540>
+#   - <https://learn.microsoft.com/windows-server/administration/openssh/openssh_install_firstuse>
+
+function InstallOpenSSHServer {
+    $OpenSSHServer = Get-WindowsCapability -Online | `
+            Where-Object -Property Name -Like "OpenSSH.Server*"
+    IF (-Not ($OpenSSHServer.State -eq "Installed")) {
+        Add-WindowsCapability -Online -Name $sshd.Name
+    }
+
+    $Sshd = Get-Service -Name "sshd"
+    IF (-Not ($Sshd.Status -eq "Running")) {
+        Start-Service "sshd"
+    }
+    IF (-Not ($Sshd.StartupType -eq "Automatic")) {
+        Set-Service -Name "sshd" -StartupType "Automatic"
+    }
+
+    $SshAgent = Get-Service -Name "ssh-agent"
+    IF (-Not ($SshAgent.Status -eq "Running")) {
+        Start-Service "ssh-agent"
+    }
+    IF (-Not ($SshAgent.StartupType -eq "Automatic")) {
+        Set-Service -Name "ssh-agent" -StartupType "Automatic"
+    }
+
+    Install-Module -Force OpenSSHUtils -Scope AllUsers
+}
+
+function SelfElevate {
+    Write-Host "${Warn}Installing 'sshd' requires Admin privileges${ResetAll}"
+    Write-Host "Install will continue automatically in 5 seconds..."
+    Sleep 5.0
+
+    # Self-elevate the script if required
+    $CurUser = New-Object Security.Principal.WindowsPrincipal(
+        [Security.Principal.WindowsIdentity]::GetCurrent()
+    )
+    $IsAdmin = $CurUser.IsInRole(
+        [Security.Principal.WindowsBuiltInRole]::Administrator
+    )
+    if ($IsAdmin) {
+        Return 0
+    }
+
+    $CurLoc = Get-Location
+    $CommandLine = "-File `"" + $MyInvocation.MyCommand.Path + "`" " + $MyInvocation.UnboundArguments
+    Start-Process -FilePath PowerShell.exe -Verb Runas -ArgumentList $CommandLine
+    Set-Location $CurLoc
+    Exit 0
+}
+
+SelfElevate
+InstallOpenSSHServer