diff --git a/src/generators/web/ui/components/SideBar/index.jsx b/src/generators/web/ui/components/SideBar/index.jsx
index 31461108..d64fa13c 100644
--- a/src/generators/web/ui/components/SideBar/index.jsx
+++ b/src/generators/web/ui/components/SideBar/index.jsx
@@ -2,7 +2,7 @@ import Select from '@node-core/ui-components/Common/Select';
 import SideBar from '@node-core/ui-components/Containers/Sidebar';
 
 import styles from './index.module.css';
-import { STATIC_DATA } from '../../constants.mjs';
+import { STATIC_DATA, SIDEBAR_GROUPS } from '../../constants.mjs';
 
 /**
  * @typedef {Object} SideBarProps
@@ -18,6 +18,41 @@ import { STATIC_DATA } from '../../constants.mjs';
  */
 const redirect = url => (window.location.href = url);
 
+/**
+ * Builds grouped sidebar navigation from flat docPages list.
+ * Pages not matching any group are placed under "Other".
+ * @param {Array<[string, string]>} docPages - [Title, URL] pairs
+ * @returns {Array<{ groupName: string, items: Array<{ label: string, link: string }> }>}
+ */
+const buildSideBarGroups = docPages => {
+  const linkMap = new Map(docPages.map(([label, link]) => [link, label]));
+  const assigned = new Set();
+
+  const groups = SIDEBAR_GROUPS.map(({ groupName, items }) => ({
+    groupName,
+    items: items
+      .filter(link => {
+        if (linkMap.has(link)) {
+          assigned.add(link);
+          return true;
+        }
+
+        return false;
+      })
+      .map(link => ({ label: linkMap.get(link), link })),
+  })).filter(group => group.items.length > 0);
+
+  const otherItems = docPages
+    .filter(([, link]) => !assigned.has(link))
+    .map(([label, link]) => ({ label, link }));
+
+  if (otherItems.length > 0) {
+    groups.push({ groupName: 'Other', items: otherItems });
+  }
+
+  return groups;
+};
+
 /**
  * Sidebar component for MDX documentation with version selection and page navigation
  * @param {SideBarProps} props - Component props
@@ -25,25 +60,17 @@ const redirect = url => (window.location.href = url);
 export default ({ versions, pathname, currentVersion, docPages }) => (
   <SideBar
     pathname={pathname}
-    groups={[
-      {
-        groupName: 'API Documentation',
-        items: docPages.map(([label, link]) => ({ label, link })),
-      },
-    ]}
+    groups={buildSideBarGroups(docPages)}
     onSelect={redirect}
     as={props => <a {...props} rel="prefetch" />}
     title="Navigation"
   >
-    <div>
-      <Select
-        label={`${STATIC_DATA.title} version`}
-        values={versions}
-        inline={true}
-        className={styles.select}
-        placeholder={currentVersion}
-        onChange={redirect}
-      />
-    </div>
+    <Select
+      label={`${STATIC_DATA.title} version`}
+      values={versions}
+      className={styles.select}
+      placeholder={currentVersion}
+      onChange={redirect}
+    />
   </SideBar>
 );
diff --git a/src/generators/web/ui/constants.mjs b/src/generators/web/ui/constants.mjs
index 2d1b5802..be4ded1a 100644
--- a/src/generators/web/ui/constants.mjs
+++ b/src/generators/web/ui/constants.mjs
@@ -1,2 +1,120 @@
 // eslint-disable-next-line no-undef
 export const STATIC_DATA = __STATIC_DATA__;
+
+/**
+ * Defines the sidebar navigation groups and their associated page URLs.
+ * Pages not listed here will be placed under "Other".
+ * @type {Array<{ groupName: string, items: Array<string> }>}
+ */
+export const SIDEBAR_GROUPS = [
+  {
+    groupName: 'Getting Started',
+    items: [
+      'documentation.html',
+      'synopsis.html',
+      'cli.html',
+      'environment_variables.html',
+      'globals.html',
+    ],
+  },
+  {
+    groupName: 'Module System',
+    items: [
+      'modules.html',
+      'esm.html',
+      'module.html',
+      'packages.html',
+      'typescript.html',
+    ],
+  },
+  {
+    groupName: 'Networking & Protocols',
+    items: [
+      'http.html',
+      'http2.html',
+      'https.html',
+      'net.html',
+      'dns.html',
+      'dgram.html',
+    ],
+  },
+  {
+    groupName: 'File System & I/O',
+    items: [
+      'fs.html',
+      'path.html',
+      'buffer.html',
+      'stream.html',
+      'string_decoder.html',
+      'zlib.html',
+      'readline.html',
+      'tty.html',
+    ],
+  },
+  {
+    groupName: 'Asynchronous Programming',
+    items: [
+      'async_context.html',
+      'async_hooks.html',
+      'events.html',
+      'timers.html',
+      'webstreams.html',
+    ],
+  },
+  {
+    groupName: 'Process & Concurrency',
+    items: [
+      'process.html',
+      'child_process.html',
+      'cluster.html',
+      'worker_threads.html',
+      'os.html',
+    ],
+  },
+  {
+    groupName: 'Security & Cryptography',
+    items: ['crypto.html', 'webcrypto.html', 'permissions.html', 'tls.html'],
+  },
+  {
+    groupName: 'Data & URL Utilities',
+    items: ['url.html', 'querystring.html', 'punycode.html', 'util.html'],
+  },
+  {
+    groupName: 'Debugging & Diagnostics',
+    items: [
+      'debugger.html',
+      'inspector.html',
+      'console.html',
+      'report.html',
+      'tracing.html',
+      'diagnostics_channel.html',
+      'errors.html',
+    ],
+  },
+  {
+    groupName: 'Testing & Assertion',
+    items: ['test.html', 'assert.html', 'repl.html'],
+  },
+  {
+    groupName: 'Performance & Observability',
+    items: ['perf_hooks.html', 'v8.html'],
+  },
+  {
+    groupName: 'Runtime & Advanced APIs',
+    items: [
+      'vm.html',
+      'wasi.html',
+      'sqlite.html',
+      'single-executable-applications.html',
+      'intl.html',
+    ],
+  },
+  {
+    groupName: 'Native & Low-level Extensions',
+    items: ['addons.html', 'n-api.html', 'embedding.html'],
+  },
+  {
+    groupName: 'Legacy & Deprecated',
+    items: ['deprecations.html', 'domain.html'],
+  },
+];
diff --git a/src/generators/web/ui/index.css b/src/generators/web/ui/index.css
index 3b0deb3e..f2fc3aea 100644
--- a/src/generators/web/ui/index.css
+++ b/src/generators/web/ui/index.css
@@ -118,3 +118,8 @@ main {
     }
   }
 }
+
+/* Override the min-width of the select component used for version selection in the sidebar */
+[class*="select"] button[role="combobox"] {
+  min-width: initial;
+}