diff --git a/packages/playwright-core/src/tools/backend/files.ts b/packages/playwright-core/src/tools/backend/files.ts
index b7e965af6e294..44e1f5ee6badd 100644
--- a/packages/playwright-core/src/tools/backend/files.ts
+++ b/packages/playwright-core/src/tools/backend/files.ts
@@ -39,15 +39,14 @@ export const uploadFile = defineTabTool({
     if (!modalState)
       throw new Error('No file chooser visible');
 
-    if (params.paths)
-      await Promise.all(params.paths.map(filePath => response.resolveClientFilename(filePath)));
+    const paths = params.paths ? await Promise.all(params.paths.map(filePath => response.resolveClientFilename(filePath))) : undefined;
 
-    response.addCode(`await fileChooser.setFiles(${JSON.stringify(params.paths)})`);
+    response.addCode(`await fileChooser.setFiles(${JSON.stringify(paths)})`);
 
     tab.clearModalState(modalState);
     await tab.waitForCompletion(async () => {
-      if (params.paths)
-        await modalState.fileChooser.setFiles(params.paths);
+      if (paths)
+        await modalState.fileChooser.setFiles(paths);
     });
   },
 
@@ -75,12 +74,11 @@ export const drop = defineTabTool({
     response.setIncludeSnapshot();
     const { locator, resolved } = await tab.targetLocator(params);
 
-    if (params.paths)
-      await Promise.all(params.paths.map(p => response.resolveClientFilename(p)));
+    const paths = params.paths ? await Promise.all(params.paths.map(p => response.resolveClientFilename(p))) : undefined;
 
     const payload: { files?: string | string[], data?: Record<string, string> } = {};
-    if (params.paths?.length)
-      payload.files = params.paths.length === 1 ? params.paths[0] : params.paths;
+    if (paths?.length)
+      payload.files = paths.length === 1 ? paths[0] : paths;
     if (params.data)
       payload.data = params.data;
 
diff --git a/packages/playwright-core/src/tools/backend/network.ts b/packages/playwright-core/src/tools/backend/network.ts
index ded33eb582207..f2ba099099c06 100644
--- a/packages/playwright-core/src/tools/backend/network.ts
+++ b/packages/playwright-core/src/tools/backend/network.ts
@@ -257,7 +257,7 @@ async function saveResponseBody(request: playwright.Request, response: ToolRespo
   if (!body.length)
     return undefined;
   const ext = getExtensionForMimeType(httpResponse.headers()['content-type']);
-  const resolved = await response.resolveClientFile({ prefix: 'response', ext, suggestedFilename }, 'Response body');
+  const resolved = await response.resolveClientOutputFile({ prefix: 'response', ext, suggestedFilename }, 'Response body');
   await fs.promises.writeFile(resolved.fileName, body);
   return resolved.relativeName;
 }
diff --git a/packages/playwright-core/src/tools/backend/pdf.ts b/packages/playwright-core/src/tools/backend/pdf.ts
index a31a3569fda1e..19a0a8ce4f5a4 100644
--- a/packages/playwright-core/src/tools/backend/pdf.ts
+++ b/packages/playwright-core/src/tools/backend/pdf.ts
@@ -36,7 +36,7 @@ const pdf = defineTabTool({
 
   handle: async (tab, params, response) => {
     const data = await tab.page.pdf();
-    const result = await response.resolveClientFile({ prefix: 'page', ext: 'pdf', suggestedFilename: params.filename }, 'Page as pdf');
+    const result = await response.resolveClientOutputFile({ prefix: 'page', ext: 'pdf', suggestedFilename: params.filename }, 'Page as pdf');
     await response.addFileResult(result, data);
     response.addCode(`await page.pdf(${formatObject({ path: result.relativeName })});`);
   },
diff --git a/packages/playwright-core/src/tools/backend/response.ts b/packages/playwright-core/src/tools/backend/response.ts
index b5315a40c341e..d7e2563fc95cd 100644
--- a/packages/playwright-core/src/tools/backend/response.ts
+++ b/packages/playwright-core/src/tools/backend/response.ts
@@ -85,12 +85,13 @@ export class Response {
     return rel;
   }
 
-  async resolveClientFile(template: FilenameTemplate, title: string): Promise<ResolvedFile> {
+  async resolveClientOutputFile(template: FilenameTemplate, title: string): Promise<ResolvedFile> {
     let fileName: string;
     if (template.suggestedFilename)
       fileName = await this.resolveClientFilename(template.suggestedFilename);
     else
       fileName = await this._context.outputFile(template, { origin: 'llm' });
+    await fs.promises.mkdir(path.dirname(fileName), { recursive: true });
     const relativeName = this._computeRelativeTo(fileName);
     const printableLink = `- [${title}](${relativeName})`;
     return { fileName, relativeName, printableLink };
@@ -106,7 +107,7 @@ export class Response {
 
   async addResult(title: string, data: Buffer | string, file: FilenameTemplate) {
     if (file.suggestedFilename || typeof data !== 'string') {
-      const resolvedFile = await this.resolveClientFile(file, title);
+      const resolvedFile = await this.resolveClientOutputFile(file, title);
       await this.addFileResult(resolvedFile, data);
     } else {
       this.addTextResult(data);
@@ -304,7 +305,7 @@ export class Response {
     if (tabSnapshot && this._includeSnapshot !== 'none') {
       if (snapshotToFile) {
         const suggestedFilename = this._includeSnapshotFileName === '<auto>' ? undefined : this._includeSnapshotFileName;
-        const resolvedFile = await this.resolveClientFile({ prefix: 'page', ext: 'yml', suggestedFilename }, 'Snapshot');
+        const resolvedFile = await this.resolveClientOutputFile({ prefix: 'page', ext: 'yml', suggestedFilename }, 'Snapshot');
         await this._writeFile(resolvedFile, tabSnapshot.ariaSnapshot);
         addSection('Snapshot', [resolvedFile.printableLink]);
       } else if (tabSnapshot.ariaSnapshotJSON !== undefined) {
diff --git a/packages/playwright-core/src/tools/backend/screenshot.ts b/packages/playwright-core/src/tools/backend/screenshot.ts
index af0cf5e0cf706..140704ef58fbd 100644
--- a/packages/playwright-core/src/tools/backend/screenshot.ts
+++ b/packages/playwright-core/src/tools/backend/screenshot.ts
@@ -72,7 +72,7 @@ const screenshot = defineTabTool({
     const target = params.target ? await tab.targetLocator({ element: params.element, target: params.target }) : null;
     const data = target ? await target.locator.screenshot(options) : await tab.page.screenshot(options);
 
-    const resolvedFile = await response.resolveClientFile({ prefix: target ? 'element' : 'page', ext: fileType, suggestedFilename: params.filename }, `Screenshot of ${screenshotTargetLabel}`);
+    const resolvedFile = await response.resolveClientOutputFile({ prefix: target ? 'element' : 'page', ext: fileType, suggestedFilename: params.filename }, `Screenshot of ${screenshotTargetLabel}`);
 
     response.addCode(`// Screenshot ${screenshotTargetLabel} and save it as ${resolvedFile.relativeName}`);
     if (target)
diff --git a/packages/playwright-core/src/tools/backend/storage.ts b/packages/playwright-core/src/tools/backend/storage.ts
index 0308496cc8bc1..a6250131a25dc 100644
--- a/packages/playwright-core/src/tools/backend/storage.ts
+++ b/packages/playwright-core/src/tools/backend/storage.ts
@@ -35,7 +35,7 @@ const storageState = defineTool({
     const browserContext = await context.ensureBrowserContext();
     const state = await browserContext.storageState();
     const serializedState = JSON.stringify(state, null, 2);
-    const resolvedFile = await response.resolveClientFile({ prefix: 'storage-state', ext: 'json', suggestedFilename: params.filename }, 'Storage state');
+    const resolvedFile = await response.resolveClientOutputFile({ prefix: 'storage-state', ext: 'json', suggestedFilename: params.filename }, 'Storage state');
     response.addCode(`await page.context().storageState({ path: ${escapeWithQuotes(resolvedFile.relativeName)} });`);
     await response.addFileResult(resolvedFile, serializedState);
   },
diff --git a/packages/playwright-core/src/tools/backend/video.ts b/packages/playwright-core/src/tools/backend/video.ts
index ad49b09bc2d7e..f3ab617dcff39 100644
--- a/packages/playwright-core/src/tools/backend/video.ts
+++ b/packages/playwright-core/src/tools/backend/video.ts
@@ -35,7 +35,7 @@ const videoStart = defineTool({
   },
 
   handle: async (context, params, response) => {
-    const resolvedFile = await response.resolveClientFile({ prefix: 'video', ext: 'webm', suggestedFilename: params.filename }, 'Video');
+    const resolvedFile = await response.resolveClientOutputFile({ prefix: 'video', ext: 'webm', suggestedFilename: params.filename }, 'Video');
     await context.startVideoRecording(resolvedFile.fileName, { size: params.size });
     response.addTextResult('Video recording started.');
   },
@@ -59,7 +59,7 @@ const videoStop = defineTool({
       return;
     }
     for (const fileName of fileNames) {
-      const resolvedFile = await response.resolveClientFile({
+      const resolvedFile = await response.resolveClientOutputFile({
         prefix: 'video',
         ext: 'webm',
         suggestedFilename: fileName
diff --git a/tests/mcp/files.spec.ts b/tests/mcp/files.spec.ts
index 3ed6693140ff1..4456529cac0ec 100644
--- a/tests/mcp/files.spec.ts
+++ b/tests/mcp/files.spec.ts
@@ -290,6 +290,46 @@ test('file upload is restricted to cwd if no roots are configured', async ({ sta
   });
 });
 
+test('file upload resolves relative paths against the root', async ({ startClient, server }, testInfo) => {
+  const rootDir = testInfo.outputPath('workspace');
+  await fs.mkdir(rootDir, { recursive: true });
+  await fs.writeFile(path.join(rootDir, 'inside.txt'), 'Inside root');
+
+  const { client } = await startClient({
+    roots: [
+      {
+        name: 'workspace',
+        uri: `file://${rootDir}`,
+      }
+    ],
+  });
+
+  server.setContent('/', `<input type="file" />`, 'text/html');
+
+  await client.callTool({
+    name: 'browser_navigate',
+    arguments: { url: server.PREFIX },
+  });
+
+  await client.callTool({
+    name: 'browser_click',
+    arguments: {
+      element: 'Textbox',
+      target: 'e2',
+    },
+  });
+
+  // The file lives in the root, not in the server's cwd.
+  expect(await client.callTool({
+    name: 'browser_file_upload',
+    arguments: {
+      paths: ['inside.txt'],
+    },
+  })).toHaveResponse({
+    code: expect.stringContaining(JSON.stringify(path.join(rootDir, 'inside.txt'))),
+  });
+});
+
 test('file upload unrestricted when flag is set', async ({ startClient, server }, testInfo) => {
   const rootDir = testInfo.outputPath('workspace');
   await fs.mkdir(rootDir, { recursive: true });
diff --git a/tests/mcp/screenshot.spec.ts b/tests/mcp/screenshot.spec.ts
index 09775eb24cc48..b9f6ad7d2e69f 100644
--- a/tests/mcp/screenshot.spec.ts
+++ b/tests/mcp/screenshot.spec.ts
@@ -246,6 +246,31 @@ test('browser_take_screenshot (filename: "output.png")', async ({ client, server
   expect(files[0]).toMatch(/^output\.png$/);
 });
 
+test('browser_take_screenshot (filename: "sub/dir/output.png")', async ({ client, server }, testInfo) => {
+  expect(await client.callTool({
+    name: 'browser_navigate',
+    arguments: { url: server.HELLO_WORLD },
+  })).toHaveResponse({
+    code: expect.stringContaining(`page.goto('http://localhost`),
+  });
+
+  expect(await client.callTool({
+    name: 'browser_take_screenshot',
+    arguments: {
+      filename: 'sub/dir/output.png',
+    },
+  })).toEqual({
+    content: [
+      {
+        text: expect.stringContaining(`output.png`),
+        type: 'text',
+      },
+    ],
+  });
+
+  expect(fs.existsSync(testInfo.outputPath('sub', 'dir', 'output.png'))).toBeTruthy();
+});
+
 test('browser_take_screenshot (imageResponses=omit)', async ({ startClient, server }, testInfo) => {
   const outputDir = testInfo.outputPath('output');
   const { client } = await startClient({