How to Connect Outlook to OpenClaw

For personal Outlook.com accounts, IMAP is enabled by default. Verify by going to outlook.com > Settings (gear icon) > Mail > Sync email > and checking that IMAP is on. The toggle should read 'IMAP enabled'. For Microsoft 365 organizational accounts, IMAP may be disabled by your IT administrator. Contact IT to confirm IMAP is enabled for your mailbox, or check via PowerShell if you have admin rights. If your Microsoft account has two-factor authentication (2FA) enabled — which is strongly recommended — you cannot use your regular account password for IMAP. Instead, you need an App Password: a one-time-use 16-character password that works without 2FA prompts. To generate an App Password: go to account.microsoft.com > Security > Advanced security options > App passwords > Create a new app password. Name it 'OpenClaw IMAP'. Microsoft generates and displays the password — copy it immediately. This is what you will use as your password in the OpenClaw config (not your regular account password). If your account does not use 2FA (not recommended), use your regular password. Note that Microsoft may prompt you to set up 2FA; doing so improves account security.

1# Outlook IMAP server settings:
2# IMAP host: outlook.office365.com
3# IMAP port: 993 (SSL)
4# SMTP host: smtp.office365.com
5# SMTP port: 587 (STARTTLS)
6
7# For personal Outlook.com accounts:
8# IMAP host: imap-mail.outlook.com
9# IMAP port: 993 (SSL)
10# SMTP host: smtp-mail.outlook.com
11# SMTP port: 587 (STARTTLS)
12
13# Test IMAP connection (requires openssl):
14openssl s_client -connect outlook.office365.com:993 -quiet
15# Should connect and show server greeting
16# Press Ctrl+C to exit

Open `~/.openclaw/config.yaml` and add the Outlook email integration block. The config needs your email address, password or App Password, and the IMAP/SMTP server settings for your account type. Use `outlook.office365.com` for Microsoft 365 organizational accounts and `imap-mail.outlook.com` for personal Outlook.com accounts. Both use port 993 for IMAP with SSL. For SMTP, both support port 587 with STARTTLS. The `poll_interval` setting controls how often OpenClaw checks the IMAP inbox for new messages. 300 seconds (5 minutes) is a good default for most workflows — shorter intervals are possible but increase server load and may trigger Microsoft's rate limiting if set below 60 seconds. The `folders` setting specifies which IMAP folders to monitor. `INBOX` is the standard inbox. You can add `Junk`, `Drafts`, or custom folders if your workflows need to process email from those locations.

1# ~/.openclaw/config.yaml
2integrations:
3  outlook-imap:
4    # Account credentials
5    email: "your-email@outlook.com"
6    password: "YOUR_APP_PASSWORD_OR_ACCOUNT_PASSWORD"
7
8    # IMAP settings (for reading email)
9    imap_host: "imap-mail.outlook.com"   # Use outlook.office365.com for M365 org accounts
10    imap_port: 993
11    imap_ssl: true
12    folders:
13      - "INBOX"
14      # - "Junk"  # Uncomment to monitor junk folder too
15
16    # SMTP settings (for sending email)
17    smtp_host: "smtp-mail.outlook.com"   # Use smtp.office365.com for M365 org accounts
18    smtp_port: 587
19    smtp_starttls: true
20
21    # Behavior settings
22    poll_interval: 300           # Seconds between inbox checks
23    mark_as_read: false          # Mark fetched emails as read (default: false)
24    fetch_body: true             # Include email body text in queries

With the config in place, test that OpenClaw can successfully read emails from your Outlook inbox via IMAP. The test commands below use the direct IMAP query syntax that OpenClaw exposes for email integrations. Start by retrieving the most recent emails from the inbox without any filters. This confirms authentication and basic connectivity. Then test a filtered query to verify the search functionality works — this is the basis for trigger conditions in automation workflows. If the initial connection fails with an authentication error, verify you are using an App Password (not your real account password) if 2FA is enabled. If the connection times out, check that your firewall allows outbound connections on port 993. OpenClaw stores the timestamp of the last-fetched email and only returns newer messages on subsequent queries — this prevents duplicate processing in polling workflows.

1# Test reading recent emails via OpenClaw's IMAP integration
2# These commands test the integration directly from the config:
3
4# Verify IMAP connection and list folders:
5curl -v --silent imaps://imap-mail.outlook.com \
6  --user "your-email@outlook.com:YOUR_APP_PASSWORD" 2>&1 | grep '\*'
7
8# Use openssl for a more detailed IMAP test:
9openssl s_client -connect imap-mail.outlook.com:993 -quiet <<EOF
10A001 LOGIN your-email@outlook.com YOUR_APP_PASSWORD
11A002 LIST "" "*"
12A003 EXAMINE INBOX
13A004 LOGOUT
14EOF
15
16# Expected output includes:
17# OK LOGIN completed
18# INBOX details (number of messages, recent messages)
19# OK LOGOUT completed

Verify that OpenClaw can send emails from your Outlook account via SMTP. This is needed for any workflow that sends notifications, replies, or outbound messages using your Outlook account as the sender. The test below sends a message to yourself — this is the safest way to verify SMTP without accidentally sending test emails to real contacts. If you see the message arrive in your own inbox within a minute, SMTP is configured correctly. Microsoft's SMTP servers require STARTTLS on port 587 — plain text SMTP without TLS is rejected. Ensure `smtp_starttls: true` is set in your config. Port 465 with SSL is also supported; the config uses 587 with STARTTLS by default because it is more widely compatible with network firewall rules. Note that Microsoft imposes daily sending limits on SMTP: up to 300 messages per day for personal Outlook.com accounts and up to 10,000 per day for Microsoft 365 plans. For high-volume sending needs, consider the Microsoft Graph integration which has better rate limit handling.

1# Test SMTP sending with swaks (install with: brew install swaks or apt install swaks)
2swaks --to your-email@outlook.com \
3      --from your-email@outlook.com \
4      --server smtp-mail.outlook.com \
5      --port 587 \
6      --auth LOGIN \
7      --auth-user your-email@outlook.com \
8      --auth-password YOUR_APP_PASSWORD \
9      --tls \
10      --header 'Subject: OpenClaw SMTP Test' \
11      --body 'This is a test email from OpenClaw SMTP configuration.'
12
13# Alternative with openssl:
14openssl s_client -starttls smtp -connect smtp-mail.outlook.com:587 -quiet
15# Then manually type SMTP commands to test authentication

With both IMAP read and SMTP send verified, build OpenClaw workflows that use the Outlook email integration. The most common pattern is a trigger-based workflow: OpenClaw polls the IMAP inbox on the configured interval, finds new messages matching your conditions, and executes downstream actions for each match. The workflow config uses the `outlook-imap` integration key. Trigger conditions can filter by sender email, subject text, or whether an attachment is present. The email fields available in workflow actions include `subject`, `from`, `body`, `date`, and `attachments`. For notification workflows that send outbound emails in response to other trigger events — a new Calendly booking, a system alert, a scheduled digest — configure the SMTP send action directly in the actions block without a polling trigger. RapidDev's team recommends keeping inbox monitoring workflows simple at first — start with subject line filtering before adding body text analysis, since body parsing logic can get complex with HTML email formatting.

1# ~/.openclaw/config.yaml — Outlook IMAP workflow examples
2workflows:
3  outlook-subject-monitor:
4    trigger:
5      integration: outlook-imap
6      event: new-message
7      conditions:
8        - field: subject
9          contains: ["urgent", "action required", "invoice"]
10    actions:
11      - type: log
12        message: "Flagged email: {{message.subject}} from {{message.from}}"
13
14  daily-inbox-summary:
15    trigger:
16      type: schedule
17      cron: "0 9 * * MON-FRI"  # Weekdays at 9 AM
18    actions:
19      - type: integration-query
20        integration: outlook-imap
21        query: messages
22        params:
23          folder: "INBOX"
24          since_hours: 24
25          unread_only: true
26      - type: log
27        message: "You have {{result.count}} unread emails from the last 24 hours"
28
29  send-notification:
30    trigger:
31      type: manual
32    actions:
33      - type: integration-call
34        integration: outlook-imap
35        action: send-email
36        params:
37          to: "recipient@example.com"
38          subject: "OpenClaw Notification"
39          body: "This message was sent automatically by OpenClaw."