diff --git a/Makefile b/Makefile
index b5ca0f3e..5c0147ac 100755
--- a/Makefile
+++ b/Makefile
@@ -171,4 +171,8 @@ gen-api-types: gen-swagger
 	# --disable-throw-on-error
 	bunx --bun swagger-typescript-api generate --sort-types --generate-union-enums --axios --add-readonly --route-types \
 		 --responses -o ${WEBUI_DIR}/lib -n api.ts -p internal/api/v1/docs/swagger.json
-	bunx --bun prettier --config ${WEBUI_DIR}/.prettierrc --write ${WEBUI_DIR}/lib/api.ts
\ No newline at end of file
+	bunx --bun prettier --config ${WEBUI_DIR}/.prettierrc --write ${WEBUI_DIR}/lib/api.ts
+
+.PHONY: update-wiki
+update-wiki:
+	DOCS_DIR=${DOCS_DIR} bun --bun scripts/update-wiki/main.ts
diff --git a/scripts/update-wiki/.gitignore b/scripts/update-wiki/.gitignore
new file mode 100644
index 00000000..b512c09d
--- /dev/null
+++ b/scripts/update-wiki/.gitignore
@@ -0,0 +1 @@
+node_modules
\ No newline at end of file
diff --git a/scripts/update-wiki/bun.lock b/scripts/update-wiki/bun.lock
new file mode 100644
index 00000000..f618b17a
--- /dev/null
+++ b/scripts/update-wiki/bun.lock
@@ -0,0 +1,26 @@
+{
+  "lockfileVersion": 1,
+  "configVersion": 1,
+  "workspaces": {
+    "": {
+      "name": "update-wiki",
+      "devDependencies": {
+        "@types/bun": "latest",
+      },
+      "peerDependencies": {
+        "typescript": "^5",
+      },
+    },
+  },
+  "packages": {
+    "@types/bun": ["@types/bun@1.3.5", "", { "dependencies": { "bun-types": "1.3.5" } }, "sha512-RnygCqNrd3srIPEWBd5LFeUYG7plCoH2Yw9WaZGyNmdTEei+gWaHqydbaIRkIkcbXwhBT94q78QljxN0Sk838w=="],
+
+    "@types/node": ["@types/node@25.0.3", "", { "dependencies": { "undici-types": "~7.16.0" } }, "sha512-W609buLVRVmeW693xKfzHeIV6nJGGz98uCPfeXI1ELMLXVeKYZ9m15fAMSaUPBHYLGFsVRcMmSCksQOrZV9BYA=="],
+
+    "bun-types": ["bun-types@1.3.5", "", { "dependencies": { "@types/node": "*" } }, "sha512-inmAYe2PFLs0SUbFOWSVD24sg1jFlMPxOjOSSCYqUgn4Hsc3rDc7dFvfVYjFPNHtov6kgUeulV4SxbuIV/stPw=="],
+
+    "typescript": ["typescript@5.9.3", "", { "bin": { "tsc": "bin/tsc", "tsserver": "bin/tsserver" } }, "sha512-jl1vZzPDinLr9eUt3J/t7V6FgNEw9QjvBPdysz9KfQDD41fQrC2Y4vKQdiaUpFT4bXlb1RHhLpp8wtm6M5TgSw=="],
+
+    "undici-types": ["undici-types@7.16.0", "", {}, "sha512-Zz+aZWSj8LE6zoxD+xrjh4VfkIG8Ya6LvYkZqtUQGJPZjYl53ypCaUwWqo7eI0x66KBGeRo+mlBEkMSeSZ38Nw=="],
+  }
+}
diff --git a/scripts/update-wiki/main.ts b/scripts/update-wiki/main.ts
new file mode 100644
index 00000000..09918414
--- /dev/null
+++ b/scripts/update-wiki/main.ts
@@ -0,0 +1,175 @@
+import { Glob } from "bun";
+import { linkSync } from "fs";
+import { mkdir, readdir, readFile, rm, writeFile } from "fs/promises";
+import path from "path";
+
+type ImplDoc = {
+  /** Directory path relative to this repo, e.g. "internal/health/check" */
+  pkgPath: string;
+  /** File name in wiki `src/impl/`, e.g. "internal-health-check.md" */
+  docFileName: string;
+  /** Absolute source README path */
+  srcPathAbs: string;
+  /** Absolute destination doc path */
+  dstPathAbs: string;
+};
+
+const START_MARKER = "// GENERATED-IMPL-SIDEBAR-START";
+const END_MARKER = "// GENERATED-IMPL-SIDEBAR-END";
+
+function escapeRegex(s: string) {
+  return s.replace(/[.*+?^${}()|[\]\\]/g, "\\$&");
+}
+
+function escapeSingleQuotedTs(s: string) {
+  return s.replace(/\\/g, "\\\\").replace(/'/g, "\\'");
+}
+
+function sanitizeFileStemFromPkgPath(pkgPath: string) {
+  // Convert a package path into a stable filename.
+  // Example: "internal/go-oidc/example" -> "internal-go-oidc-example"
+  // Keep it readable and unique (uses full path).
+  const parts = pkgPath
+    .split("/")
+    .filter(Boolean)
+    .map((p) => p.replace(/[^A-Za-z0-9._-]+/g, "-"));
+  const joined = parts.join("-");
+  return joined.replace(/-+/g, "-").replace(/^-|-$/g, "");
+}
+
+async function listRepoReadmes(repoRootAbs: string): Promise<string[]> {
+  const glob = new Glob("**/README.md");
+  const readmes: string[] = [];
+
+  for await (const rel of glob.scan({
+    cwd: repoRootAbs,
+    onlyFiles: true,
+    dot: false,
+  })) {
+    // Bun returns POSIX-style rel paths.
+    if (rel === "README.md") continue; // exclude root README
+    if (rel.startsWith(".git/") || rel.includes("/.git/")) continue;
+    if (rel.startsWith("node_modules/") || rel.includes("/node_modules/"))
+      continue;
+    if (rel.startsWith("internal/go-oidc/")) continue;
+    if (rel.startsWith("internal/gopsutil/")) continue;
+    readmes.push(rel);
+  }
+
+  // Deterministic order.
+  readmes.sort((a, b) => a.localeCompare(b));
+  return readmes;
+}
+
+async function ensureHardLink(srcAbs: string, dstAbs: string) {
+  await mkdir(path.dirname(dstAbs), { recursive: true });
+  await rm(dstAbs, { force: true });
+  // Prefer sync for better error surfaces in Bun on some platforms.
+  linkSync(srcAbs, dstAbs);
+}
+
+async function syncImplDocs(
+  repoRootAbs: string,
+  wikiRootAbs: string
+): Promise<ImplDoc[]> {
+  const implDirAbs = path.join(wikiRootAbs, "src", "impl");
+  await mkdir(implDirAbs, { recursive: true });
+
+  const readmes = await listRepoReadmes(repoRootAbs);
+  const docs: ImplDoc[] = [];
+  const expectedFileNames = new Set<string>();
+
+  for (const readmeRel of readmes) {
+    const pkgPath = path.posix.dirname(readmeRel);
+    if (!pkgPath || pkgPath === ".") continue;
+
+    const docStem = sanitizeFileStemFromPkgPath(pkgPath);
+    if (!docStem) continue;
+    const docFileName = `${docStem}.md`;
+
+    const srcPathAbs = path.join(repoRootAbs, readmeRel);
+    const dstPathAbs = path.join(implDirAbs, docFileName);
+
+    await ensureHardLink(srcPathAbs, dstPathAbs);
+
+    docs.push({ pkgPath, docFileName, srcPathAbs, dstPathAbs });
+    expectedFileNames.add(docFileName);
+  }
+
+  // Clean orphaned impl docs.
+  const existing = await readdir(implDirAbs, { withFileTypes: true });
+  for (const ent of existing) {
+    if (!ent.isFile()) continue;
+    if (!ent.name.endsWith(".md")) continue;
+    if (expectedFileNames.has(ent.name)) continue;
+    await rm(path.join(implDirAbs, ent.name), { force: true });
+  }
+
+  // Deterministic for sidebar.
+  docs.sort((a, b) => a.pkgPath.localeCompare(b.pkgPath));
+  return docs;
+}
+
+function renderSidebarItems(docs: ImplDoc[], indent: string) {
+  // link: '/impl/<file>.md' because VitePress `srcDir = "src"`.
+  if (docs.length === 0) return "";
+  return (
+    docs
+      .map((d) => {
+        const text = escapeSingleQuotedTs(d.pkgPath);
+        const link = escapeSingleQuotedTs(`/impl/${d.docFileName}`);
+        return `${indent}{ text: '${text}', link: '${link}' },`;
+      })
+      .join("\n") + "\n"
+  );
+}
+
+async function updateVitepressSidebar(wikiRootAbs: string, docs: ImplDoc[]) {
+  const configPathAbs = path.join(wikiRootAbs, ".vitepress", "config.mts");
+  if (!(await Bun.file(configPathAbs).exists())) {
+    throw new Error(`vitepress config not found: ${configPathAbs}`);
+  }
+
+  const original = await readFile(configPathAbs, "utf8");
+
+  // Replace between markers with generated items.
+  // We keep indentation based on the marker line.
+  const markerRe = new RegExp(
+    `(^[\\t ]*)${escapeRegex(START_MARKER)}[\\s\\S]*?\\n\\1${escapeRegex(
+      END_MARKER
+    )}`,
+    "m"
+  );
+
+  const m = original.match(markerRe);
+  if (!m) {
+    throw new Error(
+      `sidebar markers not found in ${configPathAbs}. Expected lines: ${START_MARKER} ... ${END_MARKER}`
+    );
+  }
+  const indent = m[1] ?? "";
+  const generated = `${indent}${START_MARKER}\n${renderSidebarItems(
+    docs,
+    indent
+  )}${indent}${END_MARKER}`;
+
+  const updated = original.replace(markerRe, generated);
+  if (updated !== original) {
+    await writeFile(configPathAbs, updated);
+  }
+}
+
+async function main() {
+  // This script lives in `scripts/update-wiki/`, so repo root is two levels up.
+  const repoRootAbs = path.resolve(import.meta.dir, "../..");
+
+  // Required by task, but allow overriding via env for convenience.
+  const wikiRootAbs = Bun.env.DOCS_DIR
+    ? path.resolve(repoRootAbs, Bun.env.DOCS_DIR)
+    : path.resolve(repoRootAbs, "..", "godoxy-webui", "wiki");
+
+  const docs = await syncImplDocs(repoRootAbs, wikiRootAbs);
+  await updateVitepressSidebar(wikiRootAbs, docs);
+}
+
+await main();
diff --git a/scripts/update-wiki/package.json b/scripts/update-wiki/package.json
new file mode 100644
index 00000000..b5aec0d0
--- /dev/null
+++ b/scripts/update-wiki/package.json
@@ -0,0 +1,10 @@
+{
+  "name": "update-wiki",
+  "private": true,
+  "devDependencies": {
+    "@types/bun": "latest"
+  },
+  "peerDependencies": {
+    "typescript": "^5"
+  }
+}
diff --git a/scripts/update-wiki/tsconfig.json b/scripts/update-wiki/tsconfig.json
new file mode 100644
index 00000000..bfa0fead
--- /dev/null
+++ b/scripts/update-wiki/tsconfig.json
@@ -0,0 +1,29 @@
+{
+  "compilerOptions": {
+    // Environment setup & latest features
+    "lib": ["ESNext"],
+    "target": "ESNext",
+    "module": "Preserve",
+    "moduleDetection": "force",
+    "jsx": "react-jsx",
+    "allowJs": true,
+
+    // Bundler mode
+    "moduleResolution": "bundler",
+    "allowImportingTsExtensions": true,
+    "verbatimModuleSyntax": true,
+    "noEmit": true,
+
+    // Best practices
+    "strict": true,
+    "skipLibCheck": true,
+    "noFallthroughCasesInSwitch": true,
+    "noUncheckedIndexedAccess": true,
+    "noImplicitOverride": true,
+
+    // Some stricter flags (disabled by default)
+    "noUnusedLocals": false,
+    "noUnusedParameters": false,
+    "noPropertyAccessFromIndexSignature": false
+  }
+}