diff --git a/packages/playwright-core/src/tools/backend/context.ts b/packages/playwright-core/src/tools/backend/context.ts
index 068e8e8339dd5..1ab516d9a7a9d 100644
--- a/packages/playwright-core/src/tools/backend/context.ts
+++ b/packages/playwright-core/src/tools/backend/context.ts
@@ -22,7 +22,7 @@ import debug from 'debug';
 import { escapeWithQuotes } from '@isomorphic/stringUtils';
 import { disposeAll } from '@isomorphic/disposable';
 import { eventsHelper } from '@utils/eventsHelper';
-import { isPathInside, isSystemDirectory, isWritable } from '@utils/fileUtils';
+import { isPathInside, isSystemDirectory, isWritable, resolveSymlinks } from '@utils/fileUtils';
 import { playwright } from '../../inprocess';
 
 import { dedent, languageGeneratorId, secretCode } from './codegen';
@@ -467,6 +467,12 @@ async function checkFile(options: ContextOptions, resolvedFilename: string, flag
   // Trust llm to use valid characters in file names.
   const output = outputDir(options);
   const workspace = options.cwd;
-  if (!isPathInside(output, resolvedFilename) && !isPathInside(workspace, resolvedFilename))
+  // Follow symlinks, an unresolvable root cannot be traversed anyway.
+  const [realOutput, realWorkspace, realFilename] = await Promise.all([
+    resolveSymlinks(output).catch(() => output),
+    resolveSymlinks(workspace).catch(() => workspace),
+    resolveSymlinks(resolvedFilename),
+  ]);
+  if (!isPathInside(realOutput, realFilename) && !isPathInside(realWorkspace, realFilename))
     throw new Error(`File access denied: ${resolvedFilename} is outside allowed roots. Allowed roots: ${output}, ${workspace}`);
 }
diff --git a/packages/utils/fileUtils.ts b/packages/utils/fileUtils.ts
index 613f298cc4a8a..12c72160be3dd 100644
--- a/packages/utils/fileUtils.ts
+++ b/packages/utils/fileUtils.ts
@@ -88,6 +88,7 @@ export function trimLongString(s: string, length = 100) {
   return s.substring(0, start) + middle + s.slice(-end);
 }
 
+// Does not follow symlinks, see resolveSymlinks.
 export function isPathInside(root: string, candidate: string): boolean {
   const resolvedRoot = path.resolve(root);
   const resolvedCandidate = path.resolve(candidate);
@@ -96,6 +97,19 @@ export function isPathInside(root: string, candidate: string): boolean {
   return resolvedCandidate.startsWith(resolvedRoot + path.sep);
 }
 
+// Like realpath, but tolerates a non-existent tail.
+export async function resolveSymlinks(filePath: string): Promise<string> {
+  const resolved = path.resolve(filePath);
+  try {
+    return await fs.promises.realpath(resolved);
+  } catch (e) {
+    const parent = path.dirname(resolved);
+    if (e.code !== 'ENOENT' || parent === resolved)
+      throw e;
+    return path.join(await resolveSymlinks(parent), path.basename(resolved));
+  }
+}
+
 export function resolveWithinRoot(root: string, fileName: string): string | null {
   if (path.isAbsolute(fileName))
     return null;
diff --git a/tests/mcp/files.spec.ts b/tests/mcp/files.spec.ts
index 4456529cac0ec..583923a56a04f 100644
--- a/tests/mcp/files.spec.ts
+++ b/tests/mcp/files.spec.ts
@@ -377,6 +377,63 @@ test('file upload unrestricted when flag is set', async ({ startClient, server }
   });
 });
 
+test('file upload follows symlinks when checking workspace roots', async ({ startClient, server }, testInfo) => {
+  test.skip(process.platform === 'win32', 'Creating symlinks requires elevated privileges on Windows');
+
+  const rootDir = testInfo.outputPath('workspace');
+  await fs.mkdir(rootDir, { recursive: true });
+  const fileInsideRoot = path.join(rootDir, 'inside.txt');
+  await fs.writeFile(fileInsideRoot, 'Inside root');
+  await fs.symlink(fileInsideRoot, path.join(rootDir, 'inside-link.txt'));
+  const fileOutsideRoot = testInfo.outputPath('outside.txt');
+  await fs.writeFile(fileOutsideRoot, 'Outside root');
+  await fs.symlink(fileOutsideRoot, path.join(rootDir, 'outside-link.txt'));
+  // Root reached through a symlink, like /tmp on macOS.
+  const rootLink = testInfo.outputPath('workspace-link');
+  await fs.symlink(rootDir, rootLink);
+
+  const { client } = await startClient({
+    roots: [
+      {
+        name: 'workspace',
+        uri: `file://${rootLink}`,
+      }
+    ],
+  });
+
+  server.setContent('/', `<input type="file" />`, 'text/html');
+  await client.callTool({
+    name: 'browser_navigate',
+    arguments: { url: server.PREFIX },
+  });
+  await client.callTool({
+    name: 'browser_click',
+    arguments: { element: 'Textbox', target: 'e2' },
+  });
+
+  // Should succeed - symlink points inside the root
+  expect(await client.callTool({
+    name: 'browser_file_upload',
+    arguments: { paths: ['inside-link.txt'] },
+  })).toHaveResponse({
+    code: expect.stringContaining(JSON.stringify(path.join(rootLink, 'inside-link.txt'))),
+  });
+
+  await client.callTool({
+    name: 'browser_click',
+    arguments: { element: 'Textbox', target: 'e2' },
+  });
+
+  // Should fail - symlink points outside the root
+  expect(await client.callTool({
+    name: 'browser_file_upload',
+    arguments: { paths: ['outside-link.txt'] },
+  })).toHaveResponse({
+    isError: true,
+    error: expect.stringMatching('File access denied: .* is outside allowed roots'),
+  });
+});
+
 const dropzoneHtml = `
   <div id="dropzone" aria-label="dropzone" style="width:300px;height:200px;border:2px dashed #888"></div>
   <script>