diff --git a/README.md b/README.md
index f394d5f367..5f02b6a91c 100644
--- a/README.md
+++ b/README.md
@@ -90,42 +90,98 @@ bun upgrade --canary
   - [What is Bun?](https://bun.sh/docs/index)
   - [Installation](https://bun.sh/docs/installation)
   - [Quickstart](https://bun.sh/docs/quickstart)
-- CLI
-  - [`bun run`](https://bun.sh/docs/cli/run)
-  - [`bun install`](https://bun.sh/docs/cli/install)
-  - [`bun test`](https://bun.sh/docs/cli/test)
+  - [TypeScript](https://bun.sh/docs/typescript)
+
+- Templating
   - [`bun init`](https://bun.sh/docs/cli/init)
   - [`bun create`](https://bun.sh/docs/cli/bun-create)
-  - [`bunx`](https://bun.sh/docs/cli/bunx)
+
 - Runtime
-  - [Runtime](https://bun.sh/docs/runtime/index)
+  - [`bun run`](https://bun.sh/docs/cli/run)
+  - [File types](https://bun.sh/docs/runtime/loaders)
+  - [TypeScript](https://bun.sh/docs/runtime/typescript)
+  - [JSX](https://bun.sh/docs/runtime/jsx)
+  - [Environment variables](https://bun.sh/docs/runtime/env)
+  - [Bun APIs](https://bun.sh/docs/runtime/bun-apis)
+  - [Web APIs](https://bun.sh/docs/runtime/web-apis)
+  - [Node.js compatibility](https://bun.sh/docs/runtime/nodejs-apis)
+  - [Single-file executable](https://bun.sh/docs/bundler/executables)
+  - [Plugins](https://bun.sh/docs/runtime/plugins)
+  - [Watch mode](https://bun.sh/docs/runtime/hot)
   - [Module resolution](https://bun.sh/docs/runtime/modules)
-  - [Hot & live reloading](https://bun.sh/docs/runtime/hot)
+  - [Auto-install](https://bun.sh/docs/runtime/autoimport)
+  - [bunfig.toml](https://bun.sh/docs/runtime/bunfig)
+  - [Debugger](https://bun.sh/docs/runtime/debugger)
+  - [Framework API](https://bun.sh/docs/runtime/framework)
+
+- Package manager
+  - [`bun install`](https://bun.sh/docs/cli/install)
+  - [`bun add`](https://bun.sh/docs/cli/add)
+  - [`bun remove`](https://bun.sh/docs/cli/remove)
+  - [`bun update`](https://bun.sh/docs/cli/update)
+  - [`bun link`](https://bun.sh/docs/cli/link)
+  - [`bun pm`](https://bun.sh/docs/cli/pm)
+  - [Global cache](https://bun.sh/docs/install/cache)
+  - [Workspaces](https://bun.sh/docs/install/workspaces)
+  - [Lifecycle scripts](https://bun.sh/docs/install/lifecycle)
+  - [Filter](https://bun.sh/docs/cli/filter)
+  - [Lockfile](https://bun.sh/docs/install/lockfile)
+  - [Scopes and registries](https://bun.sh/docs/install/registries)
+  - [Overrides and resolutions](https://bun.sh/docs/install/overrides)
+
+- Bundler
+  - [`Bun.build`](https://bun.sh/docs/bundler)
+  - [Loaders](https://bun.sh/docs/bundler/loaders)
   - [Plugins](https://bun.sh/docs/bundler/plugins)
-- Ecosystem
-  - [Node.js](https://bun.sh/docs/ecosystem/nodejs)
-  - [TypeScript](https://bun.sh/docs/ecosystem/typescript)
-  - [React](https://bun.sh/docs/ecosystem/react)
-  - [Elysia](https://bun.sh/docs/ecosystem/elysia)
-  - [Hono](https://bun.sh/docs/ecosystem/hono)
-  - [Express](https://bun.sh/docs/ecosystem/express)
-  - [awesome-bun](https://github.com/apvarun/awesome-bun)
+  - [Macros](https://bun.sh/docs/bundler/macros)
+  - [vs esbuild](https://bun.sh/docs/bundler/vs-esbuild)
+
+- Test runner
+  - [`bun test`](https://bun.sh/docs/cli/test)
+  - [Writing tests](https://bun.sh/docs/test/writing)
+  - [Watch mode](https://bun.sh/docs/test/hot)
+  - [Lifecycle hooks](https://bun.sh/docs/test/lifecycle)
+  - [Mocks](https://bun.sh/docs/test/mocks)
+  - [Snapshots](https://bun.sh/docs/test/snapshots)
+  - [Dates and times](https://bun.sh/docs/test/time)
+  - [DOM testing](https://bun.sh/docs/test/dom)
+  - [Code coverage](https://bun.sh/docs/test/coverage)
+
+- Package runner
+  - [`bunx`](https://bun.sh/docs/cli/bunx)
+
 - API
-  - [HTTP](https://bun.sh/docs/api/http)
+  - [HTTP server](https://bun.sh/docs/api/http)
   - [WebSockets](https://bun.sh/docs/api/websockets)
-  - [TCP Sockets](https://bun.sh/docs/api/tcp)
+  - [Workers](https://bun.sh/docs/api/workers)
+  - [Binary data](https://bun.sh/docs/api/binary-data)
+  - [Streams](https://bun.sh/docs/api/streams)
   - [File I/O](https://bun.sh/docs/api/file-io)
+  - [import.meta](https://bun.sh/docs/api/import-meta)
   - [SQLite](https://bun.sh/docs/api/sqlite)
   - [FileSystemRouter](https://bun.sh/docs/api/file-system-router)
+  - [TCP sockets](https://bun.sh/docs/api/tcp)
+  - [UDP sockets](https://bun.sh/docs/api/udp)
   - [Globals](https://bun.sh/docs/api/globals)
-  - [Spawn](https://bun.sh/docs/api/spawn)
+  - [$ Shell](https://bun.sh/docs/runtime/shell)
+  - [Child processes](https://bun.sh/docs/api/spawn)
   - [Transpiler](https://bun.sh/docs/api/transpiler)
+  - [Hashing](https://bun.sh/docs/api/hashing)
   - [Console](https://bun.sh/docs/api/console)
   - [FFI](https://bun.sh/docs/api/ffi)
   - [HTMLRewriter](https://bun.sh/docs/api/html-rewriter)
   - [Testing](https://bun.sh/docs/api/test)
   - [Utils](https://bun.sh/docs/api/utils)
   - [Node-API](https://bun.sh/docs/api/node-api)
+  - [Glob](https://bun.sh/docs/api/glob)
+  - [Semver](https://bun.sh/docs/api/semver)
+
+- Project
+  - [Roadmap](https://bun.sh/docs/project/roadmap)
+  - [Benchmarking](https://bun.sh/docs/project/benchmarking)
+  - [Contributing](https://bun.sh/docs/project/contributing)
+  - [Building Windows](https://bun.sh/docs/project/building-windows)
+  - [License](https://bun.sh/docs/project/licensing)
 
 ## Contributing
 
diff --git a/scripts/nav2readme.ts b/scripts/nav2readme.ts
new file mode 100644
index 0000000000..6d19d42865
--- /dev/null
+++ b/scripts/nav2readme.ts
@@ -0,0 +1,40 @@
+// Regenerate the Table of Contents in the README by reading through nav.ts
+//
+// To run this:
+//
+//   bun ./scripts/nav2readme.ts
+//
+//
+import nav from "../docs/nav";
+
+function getMarkdown() {
+  let md = "";
+
+  for (const item of nav.items) {
+    if (item.type === "divider") {
+      md += "\n" + `- ${item.title}` + "\n";
+    } else {
+      md += `  - [${item.title}](https://bun.sh/docs/${item.slug})` + "\n";
+    }
+  }
+
+  return md;
+}
+
+const text = await Bun.file(Bun.fileURLToPath(import.meta.resolve("../README.md"))).text();
+const startI = text.indexOf("## Quick links\n");
+if (startI === -1) {
+  throw new Error("Could not find ## Quick links in README");
+}
+const start = startI + "## Quick links\n".length;
+
+const contributing = text.indexOf("## Contributing\n", start);
+
+if (contributing === -1) {
+  throw new Error("Could not find ## Contributing in README");
+}
+
+const combined =
+  [text.slice(0, start), getMarkdown(), text.slice(contributing)].map(text => text.trim()).join("\n\n") + "\n";
+
+await Bun.write(Bun.fileURLToPath(import.meta.resolve("../README.md")), combined);