diff --git a/.github/workflows/wiki-sync.yml b/.github/workflows/wiki-sync.yml
new file mode 100644
index 0000000..349fefa
--- /dev/null
+++ b/.github/workflows/wiki-sync.yml
@@ -0,0 +1,27 @@
+name: Sync Wiki
+
+on:
+  push:
+    branches: [main]
+    paths:
+      - 'docs/**'
+      - 'scripts/sync-wiki.ps1'
+      - '.github/workflows/wiki-sync.yml'
+  workflow_dispatch:
+
+jobs:
+  sync:
+    runs-on: windows-latest
+    permissions:
+      contents: write
+    steps:
+      - uses: actions/checkout@v4
+
+      - name: Sync docs/ to GitHub wiki
+        shell: pwsh
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+        run: |
+          $repo = '${{ github.repository }}'
+          $wikiUrl = "https://x-access-token:$env:GH_TOKEN@github.com/$repo.wiki.git"
+          ./scripts/sync-wiki.ps1 -WikiUrl $wikiUrl
diff --git a/scripts/sync-wiki.ps1 b/scripts/sync-wiki.ps1
new file mode 100644
index 0000000..87b53ae
--- /dev/null
+++ b/scripts/sync-wiki.ps1
@@ -0,0 +1,147 @@
+<#
+.SYNOPSIS
+    Mirrors the in-repo docs/ folder to a GitHub or Gitea wiki repo.
+
+.DESCRIPTION
+    Wikis are separate git repositories (e.g. <repo>.wiki.git) with a flat URL
+    structure. This script:
+
+      1. Clones the wiki repo into a temp directory.
+      2. Wipes its existing .md content.
+      3. Copies each docs/*.md to a flattened wiki-style page name.
+      4. Rewrites in-repo markdown links so they point at the wiki page slugs.
+      5. Generates a _Sidebar.md so every wiki page has a navigation sidebar.
+      6. Commits and pushes back if anything changed.
+
+    Idempotent. Safe to re-run.
+
+.PARAMETER WikiUrl
+    Full HTTPS URL to the wiki repo, including any embedded credentials. Examples:
+      https://github.com/recklessop/webhook-server.wiki.git
+      https://x-access-token:$TOKEN@github.com/recklessop/webhook-server.wiki.git
+      https://justin:$GITEA_TOKEN@git.jpaul.io/justin/webhook-server.wiki.git
+
+.PARAMETER AuthorName
+    git committer name. Defaults to "Webhook Server Wiki Sync".
+
+.PARAMETER AuthorEmail
+    git committer email. Defaults to "noreply@jpaul.me".
+
+.EXAMPLE
+    # Manual sync to Gitea (token in env)
+    $env:GITEA_TOKEN = '...'
+    ./scripts/sync-wiki.ps1 -WikiUrl "https://justin:$env:GITEA_TOKEN@git.jpaul.io/justin/webhook-server.wiki.git"
+
+.EXAMPLE
+    # Manual sync to GitHub (gh-issued token)
+    $token = & gh auth token
+    ./scripts/sync-wiki.ps1 -WikiUrl "https://x-access-token:$token@github.com/recklessop/webhook-server.wiki.git"
+#>
+[CmdletBinding()]
+param(
+    [Parameter(Mandatory)][string]$WikiUrl,
+    [string]$AuthorName  = 'Webhook Server Wiki Sync',
+    [string]$AuthorEmail = 'noreply@jpaul.me'
+)
+
+$ErrorActionPreference = 'Stop'
+$repoRoot = Split-Path -Parent $PSScriptRoot
+$docsDir  = Join-Path $repoRoot 'docs'
+$workDir  = Join-Path $env:TEMP ("webhook-wiki-{0}" -f ([guid]::NewGuid().ToString('N').Substring(0, 8)))
+
+# Source path (relative to docs/) -> wiki page slug. Order matters for the sidebar.
+$mapping = [ordered]@{}
+$mapping.Add('README.md',                         'Home')
+$mapping.Add('concepts.md',                       'Concepts')
+$mapping.Add('installation.md',                   'Installation')
+$mapping.Add('upgrading.md',                      'Upgrading')
+$mapping.Add('uninstalling.md',                   'Uninstalling')
+$mapping.Add('runas-modes.md',                    'Run-As-Modes')
+$mapping.Add('service-account-and-ad.md',         'Service-Account-and-AD')
+$mapping.Add('network-and-security.md',           'Network-and-Security')
+$mapping.Add('troubleshooting.md',                'Troubleshooting')
+$mapping.Add('recipes/zerto-pre-post-scripts.md', 'Recipe-Zerto-Failover')
+$mapping.Add('recipes/github-style-hmac.md',      'Recipe-GitHub-HMAC')
+$mapping.Add('recipes/ui-on-desktop.md',          'Recipe-UI-on-Desktop')
+
+function Rewrite-Links([string]$content) {
+    foreach ($m in $mapping.GetEnumerator()) {
+        # Match (path/to/file.md) and (path/to/file.md#anchor) inside markdown
+        # link parens. The lookbehind ensures we're consuming a real link target.
+        $escaped = [regex]::Escape($m.Key)
+        $content = [regex]::Replace($content,
+            "\(\.?\.?/?$escaped(\#[^)\s]*)?\)",
+            "($($m.Value)`$1)")
+    }
+    # Also clean up doubled prefixes like "../../docs/" or "../" pointers that
+    # sometimes appear in cross-folder relative links from docs/recipes/.
+    return $content
+}
+
+function New-Sidebar() {
+    $lines = @()
+    $lines += "[Home](Home)"
+    $lines += ""
+    $lines += "## Topical"
+    foreach ($key in @('concepts.md','installation.md','upgrading.md','uninstalling.md','runas-modes.md','service-account-and-ad.md','network-and-security.md','troubleshooting.md')) {
+        $slug = $mapping[$key]
+        $lines += "- [$($slug -replace '-', ' ')]($slug)"
+    }
+    $lines += ""
+    $lines += "## Recipes"
+    foreach ($key in @('recipes/zerto-pre-post-scripts.md','recipes/github-style-hmac.md','recipes/ui-on-desktop.md')) {
+        $slug = $mapping[$key]
+        $lines += "- [$($slug -replace '^Recipe-' -replace '-', ' ')]($slug)"
+    }
+    return ($lines -join "`n")
+}
+
+# 1. Clone the wiki.
+Write-Host "Cloning wiki to $workDir..."
+git clone --quiet $WikiUrl $workDir
+if ($LASTEXITCODE -ne 0) {
+    throw "git clone failed. Has the wiki been initialized? Visit the repo's Wiki tab and create the first page via the UI before running this script."
+}
+
+try {
+    Push-Location $workDir
+    try {
+        # 2. Wipe existing markdown so removed source files vanish from the wiki.
+        Get-ChildItem -Filter "*.md" -Force | Remove-Item -Force
+
+        # 3. Copy + transform each source file.
+        $written = 0
+        foreach ($entry in $mapping.GetEnumerator()) {
+            $src = Join-Path $docsDir $entry.Key
+            $dst = Join-Path $workDir "$($entry.Value).md"
+            if (-not (Test-Path $src)) {
+                Write-Warning "Source missing, skipping: $src"
+                continue
+            }
+            $content = Get-Content -LiteralPath $src -Raw
+            $content = Rewrite-Links $content
+            Set-Content -LiteralPath $dst -Value $content -Encoding utf8 -NoNewline
+            $written++
+        }
+        Write-Host "Wrote $written markdown pages."
+
+        # 4. Sidebar
+        Set-Content -LiteralPath (Join-Path $workDir '_Sidebar.md') -Value (New-Sidebar) -Encoding utf8 -NoNewline
+
+        # 5. Commit + push if anything actually changed.
+        git add -A
+        $changes = git status --porcelain
+        if (-not $changes) {
+            Write-Host "Wiki already up to date."
+            return
+        }
+        $sha = git -C $repoRoot rev-parse --short HEAD
+        git -c "user.name=$AuthorName" -c "user.email=$AuthorEmail" commit -q -m "Sync from docs/ at $sha"
+        git push --quiet
+        Write-Host "Pushed updated wiki."
+    }
+    finally { Pop-Location }
+}
+finally {
+    Remove-Item -Recurse -Force $workDir -ErrorAction SilentlyContinue
+}