diff --git a/src/generators/web/utils/__tests__/processing.test.mjs b/src/generators/web/utils/__tests__/processing.test.mjs
index afbc64c3..c2aa4469 100644
--- a/src/generators/web/utils/__tests__/processing.test.mjs
+++ b/src/generators/web/utils/__tests__/processing.test.mjs
@@ -1,7 +1,22 @@
 import assert from 'node:assert/strict';
 import { describe, it } from 'node:test';
 
-import { populateWithEvaluation } from '../processing.mjs';
+import {
+  default as getConfig,
+  setConfig,
+} from '../../../../utils/configuration/index.mjs';
+import { populateWithEvaluation, resolvePageRoot } from '../processing.mjs';
+
+await setConfig({
+  version: 'v22.0.0',
+  changelog: [],
+  generators: {
+    web: {
+      useAbsoluteURLs: false,
+      baseURL: 'https://nodejs.org/docs',
+    },
+  },
+});
 
 describe('populateWithEvaluation', () => {
   it('substitutes simple ${variable} placeholders', () => {
@@ -61,3 +76,30 @@ describe('populateWithEvaluation', () => {
     assert.strictEqual(result, 'count: 42');
   });
 });
+
+describe('resolvePageRoot', () => {
+  it('keeps relative roots for regular pages', () => {
+    const result = resolvePageRoot({ path: '/api/fs' });
+    assert.strictEqual(result, '../');
+  });
+
+  it('uses the server root for synthetic pages', () => {
+    const result = resolvePageRoot({
+      path: '/404',
+      synthetic: true,
+    });
+    assert.strictEqual(result, '/');
+  });
+
+  it('uses the configured base URL for synthetic pages with absolute URLs', async () => {
+    getConfig('web').useAbsoluteURLs = true;
+
+    const result = resolvePageRoot({
+      path: '/404',
+      synthetic: true,
+    });
+    assert.strictEqual(result, 'https://nodejs.org/docs/');
+
+    getConfig('web').useAbsoluteURLs = false;
+  });
+});
diff --git a/src/generators/web/utils/processing.mjs b/src/generators/web/utils/processing.mjs
index 5b528ff5..d09191b6 100644
--- a/src/generators/web/utils/processing.mjs
+++ b/src/generators/web/utils/processing.mjs
@@ -31,6 +31,20 @@ export const populateWithEvaluation = (template, config) => {
   return fn(...values);
 };
 
+/**
+ * @param {import('../../metadata/types').MetadataEntry} data
+ * @returns {string}
+ */
+export const resolvePageRoot = data => {
+  if (data.synthetic === true) {
+    const { baseURL, useAbsoluteURLs } = getConfig('web');
+    return useAbsoluteURLs ? String(baseURL).replace(/\/?$/, '/') : '/';
+  }
+
+  const unresolvedRoot = relativeOrAbsolute('/', data.path);
+  return unresolvedRoot.endsWith('/') ? unresolvedRoot : `${unresolvedRoot}/`;
+};
+
 /**
  * Converts JSX AST entries to server and client JavaScript code.
  *
@@ -131,10 +145,7 @@ export async function processJSXEntries(
   // Step 3: Render final HTML pages
   const results = await Promise.all(
     entries.map(async ({ data }) => {
-      const unresolvedRoot = relativeOrAbsolute('/', data.path);
-      const root = unresolvedRoot.endsWith('/')
-        ? unresolvedRoot
-        : `${unresolvedRoot}/`;
+      const root = resolvePageRoot(data);
 
       // Replace template placeholders with actual content
       const renderedHtml = populateWithEvaluation(template, {