Outlook Web

Outlook Web Access Skill

This skill provides access to Outlook Web (outlook.office.com) via playwright-cli with persistent session management.

Session Configuration

All commands must use: --session=outlook-web

This ensures cookies and authentication persist between commands.

First-Time Authentication

Microsoft login requires manual intervention. Follow these steps for first-time setup:

Step 1: Open Outlook in headed mode to trigger login

playwright-cli open "https://outlook.office.com/mail/inbox" --session=outlook-web --headed

The browser will open visibly and redirect to Microsoft login. Tell the user to complete login manually in the opened browser window.

Step 2: Verify authentication

After user confirms login is complete:

playwright-cli snapshot --session=outlook-web

If successful, the snapshot will show inbox content (email subjects, folders). If it shows a login form, authentication is not complete.

Note: After initial authentication, subsequent commands can run headless (default) since the session cookies persist.

Detecting Session Expiry

Microsoft sessions expire after ~7-14 days. Signs of expiry:

• Snapshot shows login form instead of inbox
• Navigation redirects to login URL

To re-authenticate: Open Outlook in headed mode again:

playwright-cli open "https://outlook.office.com/mail/inbox" --session=outlook-web --headed

Complete the login manually in the browser window.

Key URLs

Base: https://outlook.office.com

Email:
- /mail/inbox           - Inbox
- /mail/drafts          - Drafts folder
- /mail/sentitems       - Sent folder
- /mail/deleteditems    - Deleted/Trash
- /mail/archive         - Archive
- /mail/junkemail       - Junk/Spam
- /mail/search?q=TERM   - Search results
- /mail/deeplink/compose - New email composer

Calendar:
- /calendar             - Calendar view
- /calendar/view/day    - Day view
- /calendar/view/week   - Week view
- /calendar/view/month  - Month view

Email Operations

View Inbox

playwright-cli open "https://outlook.office.com/mail/inbox" --session=outlook-web
playwright-cli snapshot --session=outlook-web

Read an Email

Navigate to inbox, then click on an email row to select it:

playwright-cli click "EMAIL_SUBJECT_OR_SELECTOR" --session=outlook-web
playwright-cli snapshot --session=outlook-web

The reading pane will show the email content.

Compose New Email (Draft by Default)

playwright-cli open "https://outlook.office.com/mail/deeplink/compose" --session=outlook-web
playwright-cli snapshot --session=outlook-web

Fill in fields:

# Add recipient
playwright-cli fill "[aria-label='To']" "recipient@example.com" --session=outlook-web

# Add subject
playwright-cli fill "[aria-label='Add a subject']" "Subject line" --session=outlook-web

# Add body (the editor area)
playwright-cli fill "[aria-label='Message body']" "Email content here" --session=outlook-web

IMPORTANT: By default, save as draft instead of sending:

# Save as draft (Ctrl+S or close the compose window)
playwright-cli keyboard "Control+s" --session=outlook-web

Only send if user explicitly requests:

# Send email (only when explicitly requested by user)
playwright-cli click "[aria-label='Send']" --session=outlook-web

Reply to an Email

Method 1: Via Reading Pane (Simple)

With an email open in the reading pane:

# Click Reply button
playwright-cli click "[aria-label='Reply']" --session=outlook-web

# Fill reply message
playwright-cli fill "[aria-label='Message body']" "Your reply text here" --session=outlook-web

# Save as draft (auto-saves, or use Ctrl+S)
playwright-cli press "Control+s" --session=outlook-web

Method 2: Complete Reply Flow

From inbox to draft reply:

# 1. Navigate to inbox
playwright-cli open "https://outlook.office.com/mail/inbox" --session=outlook-web

# 2. Click the email (get ref from snapshot)
playwright-cli snapshot --session=outlook-web
playwright-cli click <email-ref> --session=outlook-web

# 3. Click Reply button
playwright-cli snapshot --session=outlook-web
playwright-cli click <reply-button-ref> --session=outlook-web

# 4. Fill reply
playwright-cli fill <message-body-ref> "Your reply message" --session=outlook-web

# 5. Save draft (Ctrl+S or Escape)
playwright-cli press "Control+s" --session=outlook-web

Method 3: Fast Batch Reply

Using run-code for speed:

playwright-cli run-code "
  await page.goto('https://outlook.office.com/mail/inbox');
  await page.getByRole('option').first().click();
  await page.getByRole('button', { name: 'Reply', exact: true }).click();
  await page.getByRole('textbox', { name: 'Message body' }).fill('Your reply');
  await page.keyboard.press('Control+s');
" --session=outlook-web

Note: Replies are auto-saved as drafts and have "Re: [Original Subject]" format.

Forward an Email

playwright-cli click "[aria-label='Forward']" --session=outlook-web
playwright-cli snapshot --session=outlook-web
# Add recipient and content

Delete an Email

With an email selected:

playwright-cli click "[aria-label='Delete']" --session=outlook-web

Search Emails

playwright-cli open "https://outlook.office.com/mail/search?q=YOUR_SEARCH_TERM" --session=outlook-web
playwright-cli snapshot --session=outlook-web

Or use the search box:

playwright-cli click "[aria-label='Search']" --session=outlook-web
playwright-cli fill "[aria-label='Search']" "search query" --session=outlook-web
playwright-cli keyboard "Enter" --session=outlook-web
playwright-cli snapshot --session=outlook-web

Navigate Folders

# Drafts
playwright-cli open "https://outlook.office.com/mail/drafts" --session=outlook-web

# Sent
playwright-cli open "https://outlook.office.com/mail/sentitems" --session=outlook-web

# Deleted
playwright-cli open "https://outlook.office.com/mail/deleteditems" --session=outlook-web

Calendar Operations

View Calendar

playwright-cli open "https://outlook.office.com/calendar" --session=outlook-web
playwright-cli snapshot --session=outlook-web

View Specific Time Range

# Day view
playwright-cli open "https://outlook.office.com/calendar/view/day" --session=outlook-web

# Week view
playwright-cli open "https://outlook.office.com/calendar/view/week" --session=outlook-web

# Month view
playwright-cli open "https://outlook.office.com/calendar/view/month" --session=outlook-web

View Event Details

Click on an event in the calendar view:

playwright-cli click "EVENT_TITLE_OR_SELECTOR" --session=outlook-web
playwright-cli snapshot --session=outlook-web

Best Practices

1. Always snapshot after navigation - Outlook loads asynchronously; snapshot confirms content is ready
2. Wait if needed - If snapshot shows loading state, wait and snapshot again:

   playwright-cli wait 2000 --session=outlook-web
   playwright-cli snapshot --session=outlook-web
   

3. Use ARIA labels - Outlook has good ARIA labeling; prefer [aria-label='...'] selectors
4. Check for errors - If an operation fails, snapshot to see current state
5. Default to drafts - Never send emails without explicit user confirmation

Advanced Usage & Optimizations

Batch Operations with run-code

For faster programmatic operations, batch multiple commands using run-code:

playwright-cli run-code "
  // Open inbox and reply to first email
  await page.goto('https://outlook.office.com/mail/inbox');
  await page.getByRole('option').first().click();
  await page.getByRole('button', { name: 'Reply', exact: true }).click();
  await page.getByRole('textbox', { name: 'Message body' }).fill('Your reply text');
  await page.keyboard.press('Control+s');
" --session=outlook-web

Benefits: 60-70% faster than individual commands, single process invocation.

Direct Email Navigation

If you have an email ID (from URL or previous snapshot), navigate directly:

# Instead of: inbox → find → click
playwright-cli open "https://outlook.office.com/mail/inbox/id/AAQkAGMxODI1MWVlLTgy..." --session=outlook-web

Email IDs are found in URLs when emails are open: /mail/inbox/id/<EMAIL_ID>

Skip Unnecessary Snapshots

For programmatic use, only snapshot when you need to extract data:

# Fast: No intermediate snapshots
playwright-cli open "https://outlook.office.com/mail/inbox" --session=outlook-web
playwright-cli click e600 --session=outlook-web
playwright-cli click "Reply" --session=outlook-web
playwright-cli fill "Message body" "Text" --session=outlook-web
# Only snapshot if you need to verify or extract data

Resource Blocking for Speed (Advanced)

Block images, fonts, and analytics to speed up page loads by 30-50%:

playwright-cli run-code "
  // Block non-essential resources
  await page.route('**/*', (route) => {
    const url = route.request().url();
    if (url.includes('browser.events.data.microsoft.com') ||
        url.includes('csp.microsoft.com') ||
        url.match(/\\.(png|jpg|jpeg|gif|svg|woff|woff2|ttf)$/)) {
      route.abort();
    } else {
      route.continue();
    }
  });

  // Then navigate
  await page.goto('https://outlook.office.com/mail/inbox');
" --session=outlook-web

Note: Test thoroughly as blocking resources may affect functionality.

Trust Auto-Save

Outlook Web auto-saves drafts every few seconds. For programmatic workflows:

• Skip navigating to drafts folder for verification
• Trust that draft saved if no error occurred
• Only verify when explicitly needed

Efficient Content Extraction for LLMs

Problem: Full page snapshots include 60-95% UI chrome (toolbars, navigation, wrappers) and only 5-40% actual content.

Solution: Use run-code to extract just the text you need:

# Extract email list as text (no YAML overhead)
playwright-cli run-code "
  const listbox = await page.locator('[role=\"listbox\"]');
  return await listbox.innerText();
" --session=outlook-web

# Extract just message body text
playwright-cli run-code "
  const body = await page.locator('[role=\"document\"]').first();
  return await body.innerText();
" --session=outlook-web

# Extract structured data as JSON
playwright-cli run-code "
  const emails = await page.locator('[role=\"option\"]')
    .evaluateAll(opts => opts.slice(0, 10).map(o => ({
      text: o.textContent.trim(),
      unread: o.textContent.includes('Unread')
    })));
  return JSON.stringify(emails, null, 2);
" --session=outlook-web

Benefits:

• 70-90% reduction in tokens
• Faster LLM processing
• Cleaner output (text or JSON vs YAML)

When to use:

• Full snapshots: Interactive exploration, getting element refs
• Text extraction: Reading email content, processing messages
• JSON extraction: Bulk operations, data analysis

Troubleshooting

"Browser is already in use" error

Close the existing playwright session:

playwright-cli close --session=outlook-web

Then retry the command.

Login page appears unexpectedly

Session has expired. Re-authenticate:

playwright-cli open "https://outlook.office.com/mail/inbox" --session=outlook-web --headed
# User completes login in the opened browser window

Content not loading

Wait and retry:

playwright-cli wait 3000 --session=outlook-web
playwright-cli snapshot --session=outlook-web

UI Pattern Reference

See references/ui-patterns.md for discovered element selectors and patterns specific to Outlook Web.