diff --git a/npm-shrinkwrap.json b/npm-shrinkwrap.json
index 76b366fb..27c29dbe 100644
--- a/npm-shrinkwrap.json
+++ b/npm-shrinkwrap.json
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       "resolved": "https://registry.npmjs.org/preact/-/preact-10.27.2.tgz",
       "integrity": "sha512-5SYSgFKSyhCbk6SrXyMpqjb5+MQBgfvEKE/OC+PujcY34sOpqtr+0AZQtPYx5IA6VxynQ7rUPCtKzyovpj9Bpg==",
       "license": "MIT",
+      "peer": true,
       "funding": {
         "type": "opencollective",
         "url": "https://opencollective.com/preact"
@@ -8038,14 +8033,13 @@
       "license": "MIT"
     },
     "node_modules/rolldown": {
-      "version": "1.0.0-beta.40",
-      "resolved": "https://registry.npmjs.org/rolldown/-/rolldown-1.0.0-beta.40.tgz",
-      "integrity": "sha512-VqEHbKpOgTPmQrZ4fVn4eshDQS/6g/fRpNE7cFSJY+eQLDZn4B9X61J6L+hnlt1u2uRI+pF7r1USs6S5fuWCvw==",
+      "version": "1.0.0-beta.47",
+      "resolved": "https://registry.npmjs.org/rolldown/-/rolldown-1.0.0-beta.47.tgz",
+      "integrity": "sha512-Mid74GckX1OeFAOYz9KuXeWYhq3xkXbMziYIC+ULVdUzPTG9y70OBSBQDQn9hQP8u/AfhuYw1R0BSg15nBI4Dg==",
       "license": "MIT",
       "dependencies": {
-        "@oxc-project/types": "=0.92.0",
-        "@rolldown/pluginutils": "1.0.0-beta.40",
-        "ansis": "^4.0.0"
+        "@oxc-project/types": "=0.96.0",
+        "@rolldown/pluginutils": "1.0.0-beta.47"
       },
       "bin": {
         "rolldown": "bin/cli.mjs"
@@ -8054,20 +8048,20 @@
         "node": "^20.19.0 || >=22.12.0"
       },
       "optionalDependencies": {
-        "@rolldown/binding-android-arm64": "1.0.0-beta.40",
-        "@rolldown/binding-darwin-arm64": "1.0.0-beta.40",
-        "@rolldown/binding-darwin-x64": "1.0.0-beta.40",
-        "@rolldown/binding-freebsd-x64": "1.0.0-beta.40",
-        "@rolldown/binding-linux-arm-gnueabihf": "1.0.0-beta.40",
-        "@rolldown/binding-linux-arm64-gnu": "1.0.0-beta.40",
-        "@rolldown/binding-linux-arm64-musl": "1.0.0-beta.40",
-        "@rolldown/binding-linux-x64-gnu": "1.0.0-beta.40",
-        "@rolldown/binding-linux-x64-musl": "1.0.0-beta.40",
-        "@rolldown/binding-openharmony-arm64": "1.0.0-beta.40",
-        "@rolldown/binding-wasm32-wasi": "1.0.0-beta.40",
-        "@rolldown/binding-win32-arm64-msvc": "1.0.0-beta.40",
-        "@rolldown/binding-win32-ia32-msvc": "1.0.0-beta.40",
-        "@rolldown/binding-win32-x64-msvc": "1.0.0-beta.40"
+        "@rolldown/binding-android-arm64": "1.0.0-beta.47",
+        "@rolldown/binding-darwin-arm64": "1.0.0-beta.47",
+        "@rolldown/binding-darwin-x64": "1.0.0-beta.47",
+        "@rolldown/binding-freebsd-x64": "1.0.0-beta.47",
+        "@rolldown/binding-linux-arm-gnueabihf": "1.0.0-beta.47",
+        "@rolldown/binding-linux-arm64-gnu": "1.0.0-beta.47",
+        "@rolldown/binding-linux-arm64-musl": "1.0.0-beta.47",
+        "@rolldown/binding-linux-x64-gnu": "1.0.0-beta.47",
+        "@rolldown/binding-linux-x64-musl": "1.0.0-beta.47",
+        "@rolldown/binding-openharmony-arm64": "1.0.0-beta.47",
+        "@rolldown/binding-wasm32-wasi": "1.0.0-beta.47",
+        "@rolldown/binding-win32-arm64-msvc": "1.0.0-beta.47",
+        "@rolldown/binding-win32-ia32-msvc": "1.0.0-beta.47",
+        "@rolldown/binding-win32-x64-msvc": "1.0.0-beta.47"
       }
     },
     "node_modules/run-parallel": {
@@ -8097,8 +8091,7 @@
       "version": "0.26.0",
       "resolved": "https://registry.npmjs.org/scheduler/-/scheduler-0.26.0.tgz",
       "integrity": "sha512-NlHwttCI/l5gCPR3D1nNXtWABUmBwvZpEQiD4IXSbIDq8BzLIK/7Ir5gTFSGZDUu37K5cMNp0hFtzO38sC7gWA==",
-      "license": "MIT",
-      "peer": true
+      "license": "MIT"
     },
     "node_modules/semver": {
       "version": "7.7.3",
@@ -8999,6 +8992,7 @@
       "integrity": "sha512-VUyWiTNQD7itdiMuJy+EuLEErLj3uwX/EpHQF8EOf33Dq3Ju6VW1GXm+swk6+1h7a49uv9fKZ+dft9jU7esdLA==",
       "dev": true,
       "hasInstallScript": true,
+      "peer": true,
       "dependencies": {
         "napi-postinstall": "^0.2.4"
       },
@@ -9404,6 +9398,7 @@
       "resolved": "https://registry.npmjs.org/zod/-/zod-3.24.3.tgz",
       "integrity": "sha512-HhY1oqzWCQWuUqvBFnsyrtZRhyPeR7SUGv+C4+MsisMuVfSPx8HpwWqH8tRahSlt6M3PiFAcoeFhZAqIXTxoSg==",
       "license": "MIT",
+      "peer": true,
       "funding": {
         "url": "https://github.com/sponsors/colinhacks"
       }
diff --git a/package.json b/package.json
index 93ed9753..add0728e 100644
--- a/package.json
+++ b/package.json
@@ -71,7 +71,7 @@
     "remark-parse": "^11.0.0",
     "remark-rehype": "^11.1.2",
     "remark-stringify": "^11.0.0",
-    "rolldown": "^1.0.0-beta.40",
+    "rolldown": "^1.0.0-beta.47",
     "semver": "^7.7.2",
     "shiki": "^3.15.0",
     "unified": "^11.0.5",
diff --git a/src/generators/web/constants.mjs b/src/generators/web/constants.mjs
index 92e4e4fa..4b1d2409 100644
--- a/src/generators/web/constants.mjs
+++ b/src/generators/web/constants.mjs
@@ -80,3 +80,18 @@ export const JSX_IMPORTS = {
     source: '@node-core/ui-components/Providers/NotificationProvider',
   },
 };
+
+/**
+ * Specification rules for resource hints like prerendering and prefetching.
+ * @see https://developer.mozilla.org/en-US/docs/Web/API/Speculation_Rules_API
+ */
+export const SPECULATION_RULES = {
+  // Eagerly prefetch all links that point to the API docs themselves
+  // in a moderate eagerness to improve resource loading
+  prefetch: [{ where: { href_matches: '/*' }, eagerness: 'eager' }],
+  prerender: [
+    // Eagerly prerender Sidebar links for faster navigation
+    // These will be done in a moderate eagerness (hover, likely next navigation)
+    { where: { selector_matches: '[rel~=prefetch]' }, eagerness: 'moderate' },
+  ],
+};
diff --git a/src/generators/web/index.mjs b/src/generators/web/index.mjs
index be716c1c..71f2f015 100644
--- a/src/generators/web/index.mjs
+++ b/src/generators/web/index.mjs
@@ -3,11 +3,15 @@ import { createRequire } from 'node:module';
 import { join } from 'node:path';
 
 import createASTBuilder from './utils/generate.mjs';
-import { processJSXEntry } from './utils/processing.mjs';
+import { processJSXEntries } from './utils/processing.mjs';
 
 /**
- * This generator transforms JSX AST (Abstract Syntax Tree) entries into a complete
- * web bundle, including server-side rendered HTML, client-side JavaScript, and CSS.
+ * Web generator - transforms JSX AST entries into complete web bundles.
+ *
+ * This generator processes JSX AST entries and produces:
+ * - Server-side rendered HTML pages
+ * - Client-side JavaScript with code splitting
+ * - Bundled CSS styles
  *
  * @type {GeneratorMetadata<Input, string>}
  */
@@ -18,57 +22,53 @@ export default {
   dependsOn: 'jsx-ast',
 
   /**
-   * The main generation function for the 'web' generator.
-   * It processes an array of JSX AST entries, converting each into a standalone HTML page
-   * with embedded client-side JavaScript and linked CSS.
+   * Main generation function that processes JSX AST entries into web bundles.
    *
-   * @param {import('../jsx-ast/utils/buildContent.mjs').JSXContent[]} entries
-   * @param {Partial<GeneratorOptions>} options
+   * @param {import('../jsx-ast/utils/buildContent.mjs').JSXContent[]} entries - JSX AST entries to process.
+   * @param {Partial<GeneratorOptions>} options - Generator options.
+   * @param {string} [options.output] - Output directory for generated files.
+   * @param {string} options.version - Documentation version string.
+   * @returns {Promise<Array<{html: Buffer, css: string}>>} Generated HTML and CSS.
    */
   async generate(entries, { output, version }) {
-    // Load the HTML template.
+    // Load the HTML template with placeholders
     const template = await readFile(
       new URL('template.html', import.meta.url),
       'utf-8'
     );
 
-    // These builders are responsible for converting the JSX AST into executable
-    // JavaScript code for both server-side rendering and client-side hydration.
+    // Create AST builders for server and client programs
     const astBuilders = createASTBuilder();
 
-    // This is necessary for the `executeServerCode` function to resolve modules
-    // within the dynamically executed server-side code.
+    // Create require function for resolving external packages in server code
     const requireFn = createRequire(import.meta.url);
 
-    const results = [];
-    let mainCss = '';
-
-    for (const entry of entries) {
-      const { html, css } = await processJSXEntry(
-        entry,
-        template,
-        astBuilders,
-        requireFn,
-        version
-      );
-      results.push({ html, css });
+    // Process all entries: convert JSX to HTML/CSS/JS
+    const { results, css, chunks } = await processJSXEntries(
+      entries,
+      template,
+      astBuilders,
+      requireFn,
+      { version }
+    );
 
-      // Capture the main CSS bundle from the first processed entry.
-      if (!mainCss && css) {
-        mainCss = css;
+    // Write files to disk if output directory is specified
+    if (output) {
+      // Write HTML files
+      for (const { html, api } of results) {
+        await writeFile(join(output, `${api}.html`), html, 'utf-8');
       }
 
-      // Write HTML file if output directory is specified
-      if (output) {
-        await writeFile(join(output, `${entry.data.api}.html`), html, 'utf-8');
+      // Write code-split JavaScript chunks
+      for (const chunk of chunks) {
+        await writeFile(join(output, chunk.fileName), chunk.code, 'utf-8');
       }
-    }
 
-    if (output && mainCss) {
-      const filePath = join(output, 'styles.css');
-      await writeFile(filePath, mainCss, 'utf-8');
+      // Write CSS bundle
+      await writeFile(join(output, 'styles.css'), css, 'utf-8');
     }
 
-    return results;
+    // Return HTML and CSS for each entry
+    return results.map(({ html }) => ({ html, css }));
   },
 };
diff --git a/src/generators/web/template.html b/src/generators/web/template.html
index 12f867c3..ad106dc3 100644
--- a/src/generators/web/template.html
+++ b/src/generators/web/template.html
@@ -15,10 +15,12 @@
 
   <!-- Apply theme before paint to avoid Flash of Unstyled Content -->
   <script>document.documentElement.setAttribute("data-theme",localStorage.getItem("theme")||(matchMedia("(prefers-color-scheme: dark)").matches?"dark":"light"));</script>
+  <script type="importmap">{{importMap}}</script>
+  <script type="speculationrules">{{speculationRules}}</script>
 </head>
 
 <body>
   <div id="root">{{dehydrated}}</div>
-  <script>{{clientBundleJs}}</script>
+  <script type="module" src="{{entrypoint}}"></script>
 </body>
 </html>
diff --git a/src/generators/web/ui/components/CodeBox.jsx b/src/generators/web/ui/components/CodeBox.jsx
index 76cad725..c24f9132 100644
--- a/src/generators/web/ui/components/CodeBox.jsx
+++ b/src/generators/web/ui/components/CodeBox.jsx
@@ -22,6 +22,7 @@ export const getLanguageDisplayName = language => {
 /** @param {import('react').PropsWithChildren<{ className: string }>} props */
 export default ({ className, ...props }) => {
   const matches = className?.match(/language-(?<language>[a-zA-Z]+)/);
+
   const language = matches?.groups?.language ?? '';
 
   const notify = useNotification();
@@ -30,7 +31,7 @@ export default ({ className, ...props }) => {
     await navigator.clipboard.writeText(text);
 
     notify({
-      duration: 300,
+      duration: 3000,
       message: (
         <div className="flex items-center gap-3">
           <CodeBracketIcon className={styles.icon} />
@@ -44,8 +45,9 @@ export default ({ className, ...props }) => {
     <BaseCodeBox
       onCopy={onCopy}
       language={getLanguageDisplayName(language)}
-      {...props}
+      className={className}
       buttonText="Copy to clipboard"
+      {...props}
     />
   );
 };
diff --git a/src/generators/web/ui/components/SideBar/index.jsx b/src/generators/web/ui/components/SideBar/index.jsx
index 2ab00f4e..2868f4c3 100644
--- a/src/generators/web/ui/components/SideBar/index.jsx
+++ b/src/generators/web/ui/components/SideBar/index.jsx
@@ -1,4 +1,4 @@
-import Select from '@node-core/ui-components/Common/Select/index.js';
+import Select from '@node-core/ui-components/Common/Select';
 import SideBar from '@node-core/ui-components/Containers/Sidebar';
 
 import styles from './index.module.css';
@@ -31,6 +31,7 @@ export default ({ versions, pathname, currentVersion, docPages }) => (
       },
     ]}
     onSelect={redirect}
+    as={props => <a {...props} rel="prefetch" />}
   >
     <div>
       <Select
diff --git a/src/generators/web/ui/index.css b/src/generators/web/ui/index.css
index dac478ec..9187b12f 100644
--- a/src/generators/web/ui/index.css
+++ b/src/generators/web/ui/index.css
@@ -1,4 +1,5 @@
 @import '@node-core/ui-components/styles/index.css';
+@import '@node-core/rehype-shiki/index.css';
 
 /* Fonts */
 :root {
diff --git a/src/generators/web/utils/bundle.mjs b/src/generators/web/utils/bundle.mjs
index 5aa297cf..ce492fc5 100644
--- a/src/generators/web/utils/bundle.mjs
+++ b/src/generators/web/utils/bundle.mjs
@@ -8,25 +8,33 @@ import staticData from './data.mjs';
  * Asynchronously bundles JavaScript source code (and its CSS imports),
  * targeting either browser (client) or server (Node.js) environments.
  *
- * @param {string} code - JavaScript/JSX source code to bundle.
- * @param {{ server: boolean }} options - Build configuration object.
+ * @param {Map<string, string>} codeMap - Map of {fileName: code} for all builds.
+ * @param {Object} [options] - Build configuration object.
+ * @param {boolean} [options.server=false] - Whether this is a server-side build.
  */
-export default async function bundleCode(code, { server = false } = {}) {
+export default async function bundleCode(codeMap, { server = false } = {}) {
   const result = await build({
-    // Define the entry point module name — this is virtual (not a real file).
-    // The virtual plugin will provide the actual code string under this name.
-    input: 'entrypoint.jsx',
+    // Entry points: array of virtual module names that the virtual plugin provides
+    input: Array.from(codeMap.keys()),
 
-    // Configuration for the output bundle
+    // Experimental features: import maps for client, none for server
+    experimental: {
+      chunkImportMap: !server,
+    },
+
+    // Output configuration
     output: {
       // Output module format:
       // - "cjs" for CommonJS (used in Node.js environments)
-      // - "iife" for browser environments (self-contained script tag)
-      format: server ? 'cjs' : 'iife',
+      // - "esm" for browser environments (Using Chunk Code-Splitting)
+      format: server ? 'cjs' : 'esm',
 
       // Minify output only for browser builds to optimize file size.
       // Server builds are usually not minified to preserve stack traces and debuggability.
       minify: !server,
+
+      // Within server builds we want to ensure dynamic imports get inlined whenever possible.
+      inlineDynamicImports: server,
     },
 
     // Platform informs Rolldown of the environment-specific code behavior:
@@ -41,25 +49,27 @@ export default async function bundleCode(code, { server = false } = {}) {
       ? ['preact', 'preact-render-to-string', '@node-core/ui-components']
       : [],
 
-    // Inject global compile-time constants that will be replaced in code.
-    // These are useful for tree-shaking and conditional branching.
-    // Be sure to update type declarations (`types.d.ts`) if these change.
-    define: {
-      // Static data injected directly into the bundle (as a literal or serialized JSON).
-      __STATIC_DATA__: staticData,
-
-      // Boolean flags used for conditional logic in source code:
-      // Example: `if (SERVER) {...}` or `if (CLIENT) {...}`
-      // These flags help split logic for server/client environments.
-      // Unused branches will be removed via tree-shaking.
-      SERVER: String(server),
-      CLIENT: String(!server),
-    },
+    transform: {
+      // Inject global compile-time constants that will be replaced in code.
+      // These are useful for tree-shaking and conditional branching.
+      // Be sure to update type declarations (`types.d.ts`) if these change.
+      define: {
+        // Static data injected directly into the bundle (as a literal or serialized JSON).
+        __STATIC_DATA__: staticData,
+
+        // Boolean flags used for conditional logic in source code:
+        // Example: `if (SERVER) {...}` or `if (CLIENT) {...}`
+        // These flags help split logic for server/client environments.
+        // Unused branches will be removed via tree-shaking.
+        SERVER: String(server),
+        CLIENT: String(!server),
+      },
 
-    // JSX transformation configuration.
-    // `'react-jsx'` enables the automatic JSX runtime, which doesn't require `import React`.
-    // Since we're using Preact via aliasing, this setting works well with `preact/compat`.
-    jsx: 'react-jsx',
+      // JSX transformation configuration.
+      // `'react-jsx'` enables the automatic JSX runtime, which doesn't require `import React`.
+      // Since we're using Preact via aliasing, this setting works well with `preact/compat`.
+      jsx: 'react-jsx',
+    },
 
     // Module resolution aliases.
     // This tells the bundler to use `preact/compat` wherever `react` or `react-dom` is imported.
@@ -73,35 +83,37 @@ export default async function bundleCode(code, { server = false } = {}) {
 
     // Array of plugins to apply during the build.
     plugins: [
-      // The virtual plugin lets us define a virtual file called 'entrypoint.jsx'
-      // with the contents provided by the `code` argument.
-      // This becomes the root module for the bundler.
-      virtual({
-        'entrypoint.jsx': code,
-      }),
+      // Virtual plugin: provides in-memory modules from codeMap
+      virtual(Object.fromEntries(codeMap)),
 
       // Load CSS imports via the custom plugin.
       // This plugin will collect imported CSS files and return them as `source` chunks.
       cssLoader(),
     ],
 
-    // Enable tree-shaking to eliminate unused imports, functions, and branches.
-    // This works best when all dependencies are marked as having no side effects.
-    // `sideEffects: false` in the package.json confirms this is safe to do.
+    // Enable tree-shaking to remove unused code
     treeshake: true,
 
-    // Disable writing output to disk.
-    // Instead, the compiled chunks are returned in memory (ideal for dev tools or sandboxing).
+    // Return chunks in memory instead of writing to disk
     write: false,
   });
 
-  // Destructure the result to get the output chunks.
-  // The first output is always the JavaScript entrypoint.
-  // Any additional chunks are styles (CSS).
-  const [js, ...cssFiles] = result.output;
+  // Separate CSS assets from JavaScript chunks
+  const assets = result.output.filter(c => c.type === 'asset');
+  const chunks = result.output.filter(c => c.type === 'chunk');
+
+  const importMap = assets.find(c => c.fileName === 'importmap.json');
 
   return {
-    js: js.code,
-    css: cssFiles.map(f => f.source).join(''),
+    css: assets
+      .filter(c => c.fileName.endsWith('.css'))
+      .map(f => f.source)
+      .join(''),
+    chunks: chunks.map(({ fileName, code, isEntry }) => ({
+      fileName: fileName.replace('_virtual_', ''),
+      isEntry,
+      code,
+    })),
+    importMap: importMap?.source.toString(),
   };
 }
diff --git a/src/generators/web/utils/chunks.mjs b/src/generators/web/utils/chunks.mjs
new file mode 100644
index 00000000..143dfa8c
--- /dev/null
+++ b/src/generators/web/utils/chunks.mjs
@@ -0,0 +1,43 @@
+/**
+ * Creates an enhanced require function that can resolve code-split chunks
+ * from a virtual file system before falling back to Node.js require.
+ *
+ * @param {Array<{fileName: string, code: string}>} chunks - Array of code-split chunks from bundler.
+ * @param {ReturnType<import('node:module').createRequire>} requireFn - Node.js require function for external packages.
+ */
+export function createChunkedRequire(chunks, requireFn) {
+  // Create a virtual file system from code-split chunks
+  const chunkModules = Object.fromEntries(
+    chunks.map(c => [`./${c.fileName}`, c.code])
+  );
+
+  /**
+   * Enhanced require function that resolves code-split chunks from virtual file system.
+   *
+   * @param {string} modulePath - Module path to require.
+   * @returns {*} Module exports.
+   */
+  const chunkedRequire = modulePath => {
+    // Check virtual file system first for code-split chunks
+    if (chunkModules[modulePath]) {
+      const mod = { exports: {} };
+
+      // Execute chunk code in isolated context with its own module.exports
+      const chunkFn = new Function(
+        'module',
+        'exports',
+        'require',
+        chunkModules[modulePath]
+      );
+
+      chunkFn(mod, mod.exports, chunkedRequire);
+
+      return mod.exports;
+    }
+
+    // Fall back to Node.js require for external packages
+    return requireFn(modulePath);
+  };
+
+  return chunkedRequire;
+}
diff --git a/src/generators/web/utils/generate.mjs b/src/generators/web/utils/generate.mjs
index d382f9c9..c40e2b74 100644
--- a/src/generators/web/utils/generate.mjs
+++ b/src/generators/web/utils/generate.mjs
@@ -5,44 +5,43 @@ import { JSX_IMPORTS, ROOT } from '../constants.mjs';
 /**
  * Creates an ES Module `import` statement as a string, based on parameters.
  *
- * @param {string|null} importName - The identifier to import
- * @param {string} source - The module path
- * @param {boolean} [useDefault=true] - Determines if the import is a default or named import.
+ * @param {string|null} importName - The identifier to import.
+ * @param {string} source - The module path.
+ * @param {boolean} [useDefault=true] - Whether to use default import (true) or named import (false).
+ * @returns {string} The generated import statement.
  */
 export const createImportDeclaration = (
   importName,
   source,
   useDefault = true
 ) => {
-  // '\' characters shouldn't escape the next character,
-  // but rather be treated as slashes.
+  // Escape backslashes to prevent treating them as escape characters
   source = source.replaceAll('\\', '\\\\');
 
-  // Side-effect-only import (CSS)
+  // Side-effect-only import (e.g., CSS files)
   if (!importName) {
     return `import "${source}";`;
   }
 
-  // Import default export
+  // Default import: import Name from "source"
   if (useDefault) {
     return `import ${importName} from "${source}";`;
   }
 
-  // Import named export
+  // Named import: import { Name } from "source"
   return `import { ${importName} } from "${source}";`;
 };
 
 /**
- * Factory function that returns two program generators:
- * - One for hydrating client-side React/Preact apps
- * - One for server-side rendering (SSR) to HTML
+ * Factory function that creates server and client program generators.
+ *
+ * Returns two functions that wrap JSX component code:
+ * - `buildClientProgram`: Wraps component for client-side hydration
+ * - `buildServerProgram`: Wraps component for server-side rendering
  */
 export default () => {
-  // Construct a list of `import` statements from JSX_IMPORTS
-  //
-  // TODO(@avivkeller): A known optimization opportunity exists:
-  // Some of these imports are only needed on the server (or only client).
-  // It would be more efficient to generate them conditionally.
+  // Generate import statements for all JSX components
+  // TODO: Optimize by conditionally including server-only or client-only imports
   const baseImports = Object.values(JSX_IMPORTS).map(
     ({ name, source, isDefaultExport = true }) =>
       createImportDeclaration(name, source, isDefaultExport)
@@ -50,24 +49,22 @@ export default () => {
 
   /**
    * Builds a client-side hydration program.
-   * @param {string} componentCode - Code expression representing a JSX component
+   *
+   * @param {string} componentCode - JSX component code expression.
+   * @returns {string} Complete client-side JavaScript program.
    */
   const buildClientProgram = componentCode => {
     return [
-      // JSX component imports
+      // Import all JSX components
       ...baseImports,
 
-      // Import client-side CSS styles.
-      // This ensures that styles used in the rendered app are loaded on the client.
-      // The use of `new URL(...).pathname` resolves the absolute path for `entrypoint.jsx`.
+      // Import CSS styles for client-side rendering
       createImportDeclaration(null, resolve(ROOT, './ui/index.css')),
 
-      // Import `hydrate()` from Preact — needed to attach to server-rendered HTML.
-      // This is a named import (not default), hence `false` as the third argument.
+      // Import Preact's hydrate function (named import)
       createImportDeclaration('hydrate', 'preact', false),
 
-      // Hydration call: binds the component to an element with ID "root"
-      // This assumes SSR has placed matching HTML there, which, it has.
+      // Hydrate the component into the root element
       `hydrate(${componentCode}, document.getElementById("root"));`,
     ].join('');
   };
@@ -75,18 +72,18 @@ export default () => {
   /**
    * Builds a server-side rendering (SSR) program.
    *
-   * @param {string} componentCode - Code expression representing a JSX component
+   * @param {string} componentCode - JSX component code expression.
+   * @returns {string} Complete server-side JavaScript program.
    */
   const buildServerProgram = componentCode => {
     return [
-      // JSX component imports
+      // Import all JSX components
       ...baseImports,
 
-      // Import Preact's SSR module
+      // Import Preact's SSR render function (named import)
       createImportDeclaration('render', 'preact-render-to-string', false),
 
-      // Render the component to an HTML string
-      // The output can be embedded directly into the server's HTML template
+      // Render component to HTML string and return it
       `return render(${componentCode});`,
     ].join('\n');
   };
diff --git a/src/generators/web/utils/processing.mjs b/src/generators/web/utils/processing.mjs
index 82610a90..d6474fb4 100644
--- a/src/generators/web/utils/processing.mjs
+++ b/src/generators/web/utils/processing.mjs
@@ -1,81 +1,108 @@
+import { randomUUID } from 'node:crypto';
+
 import HTMLMinifier from '@minify-html/node';
-import { toJs, jsx } from 'estree-util-to-js';
+import { jsx, toJs } from 'estree-util-to-js';
 
+import { SPECULATION_RULES } from '../constants.mjs';
 import bundleCode from './bundle.mjs';
+import { createChunkedRequire } from './chunks.mjs';
 
 /**
- * Executes server-side JavaScript code in a safe, isolated context.
- * This function takes a string of JavaScript code, bundles it, and then runs it
- * within a new Function constructor to prevent scope pollution and allow for
- * dynamic module loading via a provided `require` function.
- * The result of the server-side execution is expected to be assigned to a
- * dynamically generated variable name, which is then returned.
+ * Executes server-side JavaScript code in an isolated context with virtual module support.
+ *
+ * Takes a map of server-side JavaScript code, bundles it (which may produce code-split chunks),
+ * and executes each entry within a new Function constructor. Code-split chunks are made
+ * available via an enhanced require function that loads them from an in-memory virtual file system.
  *
- * @param {string} serverCode - The server-side JavaScript code to execute as a string.
- * @param {ReturnType<import('node:module').createRequire>} requireFn - A Node.js `require` function
+ * @param {Map<string, string>} serverCodeMap - Map of fileName to server-side JavaScript code.
+ * @param {ReturnType<import('node:module').createRequire>} requireFn - Node.js require function for external packages.
+ * @returns {Promise<Map<string, string>>} Map of fileName to dehydrated (server-rendered) HTML content.
  */
-export async function executeServerCode(serverCode, requireFn) {
-  // Bundle the server-side code. This step resolves imports and prepares the code
-  // for execution, ensuring all necessary dependencies are self-contained.
-  const { js: bundledServer } = await bundleCode(serverCode, { server: true });
-
-  // Create a new Function from the bundled server code.
-  // The `require` argument is passed into the function's scope, allowing the
-  // `bundledServer` code to use it for dynamic imports.
-  const executedFunction = new Function('require', bundledServer);
-
-  // Execute the dynamically created function with the provided `requireFn`.
-  // The result of this execution is the dehydrated content from the server-side rendering.
-  return executedFunction(requireFn);
+export async function executeServerCode(serverCodeMap, requireFn) {
+  const dehydratedMap = new Map();
+
+  // Bundle all server-side code, which may produce code-split chunks
+  const { chunks } = await bundleCode(serverCodeMap, { server: true });
+
+  const entryChunks = chunks.filter(c => c.isEntry);
+  const otherChunks = chunks.filter(c => !c.isEntry);
+
+  // Create enhanced require function that can resolve code-split chunks
+  const enhancedRequire = createChunkedRequire(otherChunks, requireFn);
+
+  // Execute each bundled entry and collect dehydrated HTML results
+  for (const chunk of entryChunks) {
+    // Create and execute function with enhanced require for chunk resolution
+    const executedFunction = new Function('require', chunk.code);
+
+    // Execute the function - result is the dehydrated HTML from server-side rendering
+    dehydratedMap.set(chunk.fileName, executedFunction(enhancedRequire));
+  }
+
+  return dehydratedMap;
 }
 
 /**
  * Processes a single JSX AST (Abstract Syntax Tree) entry to generate a complete
  * HTML page, including server-side rendered content, client-side JavaScript, and CSS.
  *
- * @param {import('../jsx-ast/utils/buildContent.mjs').JSXContent} entry - The JSX AST entry to process.
+ * @param {Array<import('../../jsx-ast/utils/buildContent.mjs').JSXContent>} entries - The JSX AST entry to process.
  * @param {string} template - The HTML template string that serves as the base for the output page.
  * @param {ReturnType<import('./generate.mjs')>} astBuilders - The AST generators
  * @param {version} version - The version to generator the documentation for
  * @param {ReturnType<import('node:module').createRequire>} requireFn - A Node.js `require` function.
  */
-export async function processJSXEntry(
-  entry,
+export async function processJSXEntries(
+  entries,
   template,
   { buildServerProgram, buildClientProgram },
   requireFn,
   { version }
 ) {
-  // `estree-util-to-js` with the `jsx` handler converts the AST nodes into a string
-  // that represents the equivalent JavaScript code, including JSX syntax.
-  const { value: code } = toJs(entry, { handlers: jsx });
-
-  // `buildServerProgram` takes the JSX-derived code and prepares it for server execution.
-  // `executeServerCode` then runs this code in a Node.js environment to produce
-  // the initial HTML content (dehydrated state) that will be sent to the client.
-  const serverCode = buildServerProgram(code);
-  const dehydrated = await executeServerCode(serverCode, requireFn);
-
-  // `buildClientProgram` prepares the JSX-derived code for client-side execution.
-  // `bundleCode` then bundles this client-side code, resolving imports and
-  // potentially generating associated CSS. This bundle will hydrate the SSR content.
-  const clientCode = buildClientProgram(code);
-  const clientBundle = await bundleCode(clientCode);
-
-  const title = `${entry.data.heading.data.name} | Node.js v${version} Documentation`;
-
-  // Replace template placeholders with actual content
-  const renderedHtml = template
-    .replace('{{title}}', title)
-    .replace('{{dehydrated}}', dehydrated ?? '')
-    .replace('{{clientBundleJs}}', () => clientBundle.js);
-
-  // The input to `minify` must be a Buffer.
-  const finalHTMLBuffer = HTMLMinifier.minify(Buffer.from(renderedHtml), {});
-
-  // Return the generated HTML and any CSS produced by the client bundle.
-  return {
-    html: finalHTMLBuffer,
-    css: clientBundle.css,
-  };
+  const serverCodeMap = new Map();
+  const clientCodeMap = new Map();
+
+  // Convert JSX AST to JavaScript for both server and client
+  for (const entry of entries) {
+    const fileName = `${entry.data.api}.jsx`;
+
+    // Convert AST to JavaScript string with JSX syntax
+    const { value: code } = toJs(entry, { handlers: jsx });
+
+    // Prepare code for server-side execution (wrapped for SSR)
+    serverCodeMap.set(fileName, buildServerProgram(code));
+
+    // Prepare code for client-side execution (wrapped for hydration)
+    clientCodeMap.set(fileName, buildClientProgram(code));
+  }
+
+  // Execute all server code at once to get dehydrated HTML
+  const serverBundle = await executeServerCode(serverCodeMap, requireFn);
+
+  // Bundle all client code at once (with code splitting for shared chunks)
+  const clientBundle = await bundleCode(clientCodeMap);
+
+  const titleSuffix = `Node.js v${version} Documentation`;
+
+  const speculationRulesString = JSON.stringify(SPECULATION_RULES, null, 2);
+
+  // Process each entry to create final HTML
+  const results = entries.map(({ data: { api, heading } }) => {
+    const fileName = `${api}.js`;
+
+    // Replace template placeholders with actual content
+    const renderedHtml = template
+      .replace('{{title}}', `${heading.data.name} | ${titleSuffix}`)
+      .replace('{{dehydrated}}', serverBundle.get(fileName) ?? '')
+      .replace('{{importMap}}', clientBundle.importMap ?? '')
+      .replace('{{entrypoint}}', `./${fileName}?${randomUUID()}`)
+      .replace('{{speculationRules}}', speculationRulesString);
+
+    // Minify HTML (input must be a Buffer)
+    const finalHTMLBuffer = HTMLMinifier.minify(Buffer.from(renderedHtml), {});
+
+    return { html: finalHTMLBuffer, api };
+  });
+
+  return { results, ...clientBundle };
 }