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Outlook - Company

Microsoft Outlook - Company Email Integration

Send emails from your own Outlook address instead of Journeybee's email service.

Why Connect Outlook?

Connecting your Microsoft Outlook account to Journeybee offers several key benefits:

  1. Professional Appearance: Emails come from your company domain (e.g., partners@yourcompany.com) instead of info@journeybee.io, making communications more recognisable and trustworthy.

  2. Better Deliverability: Emails from your domain are less likely to be flagged as spam since they're sent through your verified Microsoft account.

  3. Centralised Email History: All partner communications are tracked in your Outlook Sent folder, giving you a complete audit trail.

  4. Automatic Fallback: If Outlook disconnects or encounters issues, Journeybee automatically falls back to Gmail (if connected) or our reliable email service, ensuring your emails always get delivered.

Before You Start

To connect Outlook, you'll need:

  • ✅ A Microsoft Outlook or Microsoft 365 account (personal or business)

  • ✅ An Admin role in Journeybee (only admins can manage integrations)

  • ✅ Access to your Microsoft account credentials

How to Connect Outlook

Step 1: Navigate to Integrations

  1. Go to Settings → Integrations

  2. Find Microsoft Outlook - Company in the list

  3. Click Connect

Step 2: Authenticate with Microsoft

  1. You'll be redirected to Microsoft's login page

  2. Sign in with your Outlook/Microsoft 365 account

  3. Review the permissions Journeybee is requesting:

    • Send mail as you - Required to send emails from your account

    • Read your profile - Used to verify your email address

  4. Click Accept to grant permissions

Step 3: Verify Connection

  1. You'll be redirected back to Journeybee

  2. You should see a success message

  3. The Outlook integration card will show as Connected with your email address

Best Email to Use?

For teams of 3+ people: We recommend using a team email address like:

Why? Team addresses prevent confusion if the person managing the integration leaves, and they appear more professional than personal email addresses.

For smaller teams: Your personal Outlook email works fine.

What Emails Use Outlook?

Once connected, Outlook will be used for:

  • ✅ Lead notifications to partners

  • ✅ Partnership invitations

  • ✅ User invitations to join your workspace

  • ✅ Lead status updates and assignments

  • ✅ Deal expiration notifications

Not sent via Outlook:

  • ❌ Password resets and security emails (always sent via Journeybee's secure service)

Checking Your Email History

To verify emails are being sent through Outlook:

  1. Go to Settings → Emails

  2. Look for emails with a cyan badge that says "Outlook"

  3. Compare with emails that have a purple badge (sent via Journeybee) or blue badge (sent via Gmail)

You can also check your Outlook Sent folder to see all emails Journeybee has sent on your behalf.

Disconnecting Outlook

To disconnect your Outlook account:

  1. Go to Settings → Integrations

  2. Find Microsoft Outlook - Company

  3. Click Disconnect or Remove

Note: After disconnecting, Journeybee will automatically fall back to Gmail (if connected) or our built-in email service. No emails will be lost.

Common Problems

My emails aren't sending

Possible causes:

  • Your Outlook integration may have expired (Microsoft requires periodic re-authorization)

  • Microsoft may have flagged unusual activity

  • You've exceeded Microsoft's daily sending limits

Solution:

  1. Try disconnecting and reconnecting Outlook

  2. Check your Microsoft account for any security alerts

  3. Verify your account is in good standing (not suspended or limited)

Emails are still being sent via Journeybee

Possible causes:

  • You recently connected Outlook (it can take a few minutes to activate)

  • The integration disconnected or expired

  • You're in development mode (Outlook is disabled in dev environments)

Solution:

  1. Check Settings → Integrations to verify Outlook shows as "Connected"

  2. Look for your email address under the integration status

  3. Try sending a test email and check Settings → Emails for the cyan "Outlook" badge

Connection failed during setup

Possible causes:

  • You didn't accept all required permissions

  • Your Microsoft account has security restrictions

  • Browser cookies or pop-up blockers interfered

Solution:

  1. Make sure you accept all permissions Microsoft requests

  2. Try using a different browser or incognito/private mode

  3. Check that pop-ups are allowed for your Journeybee domain

  4. If using a work account, check with your IT administrator about app permissions

Important Notes

Privacy & Security

  • Journeybee cannot read your emails - we only have permission to send on your behalf

  • Your Outlook credentials are never stored - we use secure OAuth tokens that can be revoked anytime

  • Microsoft tokens are encrypted in our database using industry-standard AES-256-GCM encryption

  • You can revoke Journeybee's access anytime from your Microsoft account permissions page

Daily Sending Limits

Microsoft has daily sending limits that vary by account type:

  • Microsoft 365 (Business): Up to 10,000 recipients per day

  • Outlook.com (Personal): Up to 300 recipients per day

  • Exchange Online: Varies by subscription (typically 10,000/day)

If you exceed these limits, Journeybee will automatically fall back to Gmail or our email service to ensure delivery.

Tip: If you regularly send high volumes, consider using a Microsoft 365 Business account.

Professional Setup Recommendations

For the best experience:

  1. Use a team email (partners@yourcompany.com) rather than personal email

  2. Add a professional signature in your Outlook settings - it will appear on all Journeybee-sent emails

  3. Set up SPF, DKIM, and DMARC records for your domain to maximise deliverability

  4. Enable multi-factor authentication on your Microsoft account for added security

  5. Regularly check your Outlook Sent folder to monitor partner communications

Getting Help

If you're still having trouble:

  1. Check this article - Most common issues are covered above

  2. Try disconnecting and reconnecting - This solves 90% of connection issues

  3. Contact support - Email support@journeybee.io with:

  • Your Journeybee company name

  • The email address you're trying to connect

  • Screenshots of any error messages

  • What you've already tried

We typically respond within 24 hours on business days.

Frequently Asked Questions

Q: Can I connect multiple Outlook accounts? A: No, only one Outlook account can be connected per company. However, you can also connect Gmail as a backup.

Q: What happens if my Outlook token expires? A: Journeybee automatically attempts to refresh the token. If refresh fails, we'll send you a notification and fall back to Gmail or our email service.

Q: Can I use a personal <Outlook.com> account? A: Yes! Both personal <Outlook.com> accounts and business Microsoft 365 accounts are supported.

Q: Will partners see my personal email signature? A: Yes, your default Outlook signature will be included in emails sent through Journeybee.

Q: How is this different from Gmail integration? A: Functionally they're the same - both send emails from your domain. Microsoft Outlook is prioritized first, then Gmail, then Journeybee's service.

Q: Can I use this with my custom domain email? A: Yes! If your custom domain email (like partners@yourcompany.com) is hosted on Microsoft 365 or Outlook, it will work perfectly.

Q: What permissions does Journeybee request? A: We request:

  • Mail.Send - To send emails on your behalf

  • User.Read - To verify your email address

  • offline_access - To refresh your token automatically

Q: Is PKCE security implemented? A: Yes! Journeybee uses PKCE (Proof Key for Code Exchange) with SHA-256 for enhanced OAuth security, protecting against authorization code interception attacks.

Q: How long do the OAuth tokens last? A: Access tokens expire after 1 hour, but Journeybee automatically refreshes them using your refresh token. Microsoft issues a new refresh token with each refresh for enhanced security.

Technical Details

For developers and IT administrators:

OAuth Scopes

  • offline_access - Enables token refresh without user interaction

  • Mail.Send - Allows sending emails as the authenticated user

  • User.Read - Retrieves basic profile information

Security Features

  • PKCE (RFC 7636) - SHA-256 code challenge prevents authorization code interception

  • State Token Validation - Prevents CSRF attacks

  • Replay Attack Prevention - State tokens cleared immediately after use

  • Token Encryption - AES-256-GCM with PBKDF2 key derivation (100,000 iterations)

  • Automatic Token Refresh - 10-minute expiry buffer per Microsoft best practices

API Endpoints

  • OAuth Initiation: POST /api/adapters/outlook/oauth

  • OAuth Callback: GET /api/adapters/outlook/callback

  • Microsoft Graph API: https://graph.microsoft.com/v1.0/me/sendMail

Error Handling

Journeybee handles these Microsoft-specific error codes:

  • invalid_grant - Token expired/revoked (triggers re-authorization)

  • interaction_required - User consent needed

  • consent_required - Additional permissions needed

  • temporarily_unavailable - Service temporarily down (automatic retry)

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