diff --git a/.build/generate-documentation.ps1 b/.build/generate-documentation.ps1
index 0a38c2e1..4a096505 100644
--- a/.build/generate-documentation.ps1
+++ b/.build/generate-documentation.ps1
@@ -2,9 +2,26 @@
     .SYNOPSIS
         Builds the markdown documentation for the module.
     .DESCRIPTION
-        Builds the markdown documentation for the module using the PlatyPS PowerShell module.
+        Builds the markdown documentation for the module using the PlatyPS PowerShell module, generating one
+        markdown page per exported function. When -WikiPath is specified, the generated documentation is also
+        synchronized into the provided wiki checkout, matching the SdnDiagnostics.wiki repository structure:
+          - Function pages are copied/overwritten into a `functions\` subfolder of the wiki.
+          - Function pages for functions that no longer exist are removed from `functions\`.
+          - The `## Functions` section of `_SideBar.md` is regenerated with a link to every exported function.
+            Any hand-authored content above the `## Functions` heading (e.g. Home, How To Guides,
+            Troubleshooting, Learning sections) is preserved as-is.
+        Other hand-authored wiki pages (e.g. Home.md) are never touched.
+    .PARAMETER WikiPath
+        Path to a local checkout of the project's GitHub wiki repository (e.g. a checkout of
+        microsoft/SdnDiagnostics.wiki). When specified, generated documentation is synchronized into this path.
 #>
 
+[CmdletBinding()]
+param (
+    [Parameter(Mandatory = $false)]
+    [System.String]$WikiPath
+)
+
 $ErrorActionPreference = "Stop"
 
 $platyFromPoshGallery = Find-Module -Name platyPS
@@ -21,7 +38,6 @@ else {
 
 $modulePath = "$PSScriptRoot\..\src\SdnDiagnostics.psd1"
 $docPath = "$PSScriptRoot\..\.documentation\functions"
-$sideBarNav = "$PSScriptRoot\..\.documentation\_SideBar.md"
 
 if(-NOT (Test-Path -Path $docPath -PathType Container)) {
     $null = New-Item -Path $docPath -ItemType Directory -Force
@@ -41,9 +57,121 @@ if($oldArticles){
 "Generating function documentation" | Write-Host
 $null = New-MarkdownHelp -Module SdnDiagnostics -OutputFolder $docPath -NoMetadata -Force
 
+$exportedFunctions = Get-Command -Module SdnDiagnostics | Sort-Object -Property Name
 $currentFiles = Get-ChildItem -Path $docPath\* -Include *.md
-foreach($function in (Get-Command -Module SdnDiagnostics)){
+foreach($function in $exportedFunctions){
     if($function.Name -inotin ($currentFiles).BaseName){
         "Documentation not generated for {0}" -f $function.Name | Write-Host -ForegroundColor:Yellow
     }
 }
+
+if($WikiPath){
+    if(-NOT (Test-Path -Path $WikiPath -PathType Container)){
+        throw "WikiPath '$WikiPath' does not exist or is not a directory."
+    }
+
+    "Synchronizing generated documentation into wiki path '{0}'" -f $WikiPath | Write-Host
+
+    # mirrors the SdnDiagnostics.wiki repository structure, where function pages live under a
+    # `functions\` subfolder alongside other hand-authored top-level wiki pages
+    $wikiFunctionsPath = Join-Path -Path $WikiPath -ChildPath "functions"
+    if(-NOT (Test-Path -Path $wikiFunctionsPath -PathType Container)) {
+        $null = New-Item -Path $wikiFunctionsPath -ItemType Directory -Force
+    }
+
+    # a manifest of function names generated by this script on the previous run is used to identify
+    # which pages are safe to remove. Only pages that this script itself generated previously (and are
+    # no longer exported) are treated as stale -- a hand-authored page that happens to match a
+    # PowerShell approved-verb naming convention (e.g. functions\Get-Started.md) is never a candidate
+    # for removal because it will never appear in the manifest.
+    $exportedFunctionNames = $exportedFunctions.Name
+    $manifestPath = Join-Path -Path $wikiFunctionsPath -ChildPath ".generated-manifest.json"
+
+    if(Test-Path -Path $manifestPath -PathType Leaf) {
+        # ConvertFrom-Json writes its array result as a single non-enumerated pipeline object, so
+        # wrapping the whole pipeline in @(...) would double-nest it into a 1-element array containing
+        # the entire array. Assign directly instead, then coerce a single-name manifest (which
+        # ConvertFrom-Json unwraps to a plain string) into a 1-element array.
+        $previouslyGeneratedNames = Get-Content -Path $manifestPath -Raw | ConvertFrom-Json
+        if($previouslyGeneratedNames -isnot [array]) {
+            $previouslyGeneratedNames = @($previouslyGeneratedNames)
+        }
+        $staleFunctionNames = $previouslyGeneratedNames | Where-Object { $_ -inotin $exportedFunctionNames }
+        if($staleFunctionNames){
+            $staleWikiFunctionDocs = Get-ChildItem -Path "$wikiFunctionsPath\*" -Include *.md | Where-Object { $_.BaseName -iin $staleFunctionNames }
+            if($staleWikiFunctionDocs){
+                "Removing {0} stale function page(s) from wiki:" -f $staleWikiFunctionDocs.Count | Write-Host
+                $staleWikiFunctionDocs | ForEach-Object { "  - {0}" -f $_.Name | Write-Host }
+                $staleWikiFunctionDocs | Remove-Item -Force
+            }
+        }
+
+        # functions present in the exported set but not in the previous manifest are newly-added pages
+        $newFunctionNames = $exportedFunctionNames | Where-Object { $_ -inotin $previouslyGeneratedNames }
+    }
+    else {
+        "No generated-page manifest found; skipping stale page removal for this run" | Write-Host -ForegroundColor:Yellow
+        # first run: every generated page is "new" from the wiki's perspective
+        $newFunctionNames = $exportedFunctionNames
+    }
+
+    Get-ChildItem -Path "$docPath\*" -Include *.md | Copy-Item -Destination $wikiFunctionsPath -Force
+
+    # summarize exactly which articles were published to the wiki on this run so it is visible in
+    # the pipeline log without needing to inspect the wiki repository's commit diff afterwards
+    "Publishing {0} function article(s) to wiki path 'functions\':" -f $exportedFunctionNames.Count | Write-Host
+    foreach($name in $exportedFunctionNames){
+        if($name -iin $newFunctionNames){
+            "  - {0} (new)" -f $name | Write-Host -ForegroundColor:Green
+        }
+        else {
+            "  - {0}" -f $name | Write-Host
+        }
+    }
+
+    # record which function pages this script generated so a future run can safely identify stale
+    # pages without guessing based on naming convention alone
+    $exportedFunctionNames | ConvertTo-Json | Set-Content -Path $manifestPath -Force
+
+    # regenerate only the "## Functions" section of _SideBar.md, preserving any hand-authored
+    # content (Home, How To Guides, Troubleshooting Guides, Learning, etc.) above that heading
+    "Updating wiki sidebar" | Write-Host
+    $sideBarWikiPath = Join-Path -Path $WikiPath -ChildPath "_SideBar.md"
+    $functionsHeadingPattern = '^#+\s*Functions\s*$'
+
+    $prefixLines = [System.Collections.Generic.List[string]]::new()
+    if(Test-Path -Path $sideBarWikiPath -PathType Leaf) {
+        $existingSideBarLines = @(Get-Content -Path $sideBarWikiPath)
+        $headingIndex = -1
+        for($i = 0; $i -lt $existingSideBarLines.Count; $i++){
+            if($existingSideBarLines[$i] -match $functionsHeadingPattern){
+                $headingIndex = $i
+                break
+            }
+        }
+
+        if($headingIndex -ge 0){
+            if($headingIndex -gt 0){
+                $prefixLines.AddRange([string[]]$existingSideBarLines[0..($headingIndex - 1)])
+            }
+        }
+        else {
+            $prefixLines.AddRange([string[]]$existingSideBarLines)
+        }
+    }
+    else {
+        "No existing _SideBar.md found at wiki root; creating a new one" | Write-Host -ForegroundColor:Yellow
+    }
+
+    $newSideBarContent = [System.Collections.Generic.List[string]]::new()
+    $newSideBarContent.AddRange($prefixLines)
+    if($newSideBarContent.Count -gt 0 -and $newSideBarContent[$newSideBarContent.Count - 1] -ne ''){
+        $newSideBarContent.Add('')
+    }
+    $newSideBarContent.Add('## Functions')
+    foreach($function in $exportedFunctions){
+        $newSideBarContent.Add("- [$($function.Name)]($($function.Name))")
+    }
+
+    $newSideBarContent | Set-Content -Path $sideBarWikiPath -Force
+}
diff --git a/.github/workflows/publish-documentation.yml b/.github/workflows/publish-documentation.yml
new file mode 100644
index 00000000..9783a1f8
--- /dev/null
+++ b/.github/workflows/publish-documentation.yml
@@ -0,0 +1,92 @@
+name: Publish Documentation
+
+# Controls when the workflow will run
+on:
+  # Triggers the workflow on push events but only for the main branch, and only when
+  # exported function source may have changed.
+  push:
+    branches:
+      - main
+    paths:
+      - 'src/**'
+
+  # Allows you to run this workflow manually from the Actions tab
+  workflow_dispatch:
+
+# Serialize runs so concurrent pushes to main can't race on the wiki checkout/push. Runs are queued
+# (not cancelled) so every triggering commit still gets published, each one regenerating docs from
+# its own checkout after the previous run's push has completed.
+concurrency:
+  group: publish-documentation-wiki
+  cancel-in-progress: false
+
+permissions:
+  contents: read
+
+jobs:
+  publish-documentation:
+    # The type of runner that the job will run on
+    runs-on: windows-latest
+
+    permissions:
+      # required to push the generated documentation to the wiki
+      contents: write
+
+    steps:
+      - name: Harden Runner
+        uses: step-security/harden-runner@b09bb98e06d4d774595224525879c09bc6e98c40 # v2.20.1
+        with:
+          egress-policy: audit
+
+      - name: 'Checkout SdnDiagnostics'
+        uses: actions/checkout@3d3c42e5aac5ba805825da76410c181273ba90b1 # v7.0.1
+        with:
+          path: main
+
+      - name: 'Checkout SdnDiagnostics Wiki'
+        uses: actions/checkout@3d3c42e5aac5ba805825da76410c181273ba90b1 # v7.0.1
+        with:
+          repository: ${{ github.repository }}.wiki
+          path: wiki
+
+      - name: 'Generate and Sync Function Documentation'
+        run: |
+          $wikiPath = (Resolve-Path -Path .\wiki).Path
+          & .\main\.build\generate-documentation.ps1 -WikiPath $wikiPath
+        shell: powershell
+
+      - name: 'Publish to Wiki'
+        run: |
+          Set-Location -Path .\wiki
+          git config user.name "github-actions[bot]"
+          git config user.email "github-actions[bot]@users.noreply.github.com"
+          git add -A
+
+          $changes = git status --porcelain
+          if ($changes) {
+            $shortSha = "${env:GITHUB_SHA}".Substring(0, 7)
+            git commit -m "docs: sync function documentation from main@$shortSha"
+
+            # the concurrency group above serializes runs of this workflow, but the wiki can also be
+            # edited out-of-band (e.g. manually). Retry a couple of times with a rebase in that case
+            # rather than failing the run outright.
+            $pushed = $false
+            for ($attempt = 1; $attempt -le 3 -and -not $pushed; $attempt++) {
+              git push
+              if ($LASTEXITCODE -eq 0) {
+                $pushed = $true
+              }
+              elseif ($attempt -lt 3) {
+                "Push failed (attempt $attempt), pulling and retrying" | Write-Host -ForegroundColor Yellow
+                git pull --rebase
+              }
+            }
+
+            if (-not $pushed) {
+              throw "Failed to push documentation changes to the wiki after multiple attempts"
+            }
+          }
+          else {
+            "No documentation changes to publish" | Write-Host
+          }
+        shell: powershell