Email Integration
Connect Gmail or Outlook for email sync and sending across all Workestra modules.
Email Integration
Connect your Gmail or Microsoft Outlook account to send and receive emails directly from Workestra. Email powers features across CRM, Support, Recruiting, and more.
Connecting Your Account
Gmail
- Go to Settings > Integrations > Connected Accounts
- Click Connect Gmail
- Sign in with your Google account and grant permissions
- Your emails will begin syncing
Outlook / Microsoft 365
- Go to Settings > Integrations > Connected Accounts
- Click Connect Outlook
- Sign in with your Microsoft account and grant permissions
- Your emails will begin syncing
Enterprise users: The Microsoft 365 integration supports Azure AD Single Sign-On, Multi-Factor Authentication (MFA), and Conditional Access policies. Learn more about Microsoft 365 integration →
Connection Security
Both Gmail and Outlook connections use industry-standard OAuth 2.0 authentication:
| Security Feature | Gmail | Outlook |
|---|---|---|
| OAuth Version | 2.0 | 2.0 + PKCE |
| Token Encryption | AES-256-GCM | AES-256-GCM |
| Token Storage | Encrypted at rest | Encrypted at rest |
| Access Scope | Read/Send email only | Read/Send email only |
| Password Access | Never | Never |
Workestra never sees or stores your email password. We use secure OAuth tokens that you can revoke at any time.
What Email Enables
Once connected, email powers features across modules:
| Module | Capabilities |
|---|---|
| CRM | Send emails from contact/deal pages, view email history, track opens |
| Support | Email-to-ticket processing, reply from ticket detail |
| Recruiting | Send outreach emails, receive applications |
| Inbox | Email notifications and activity feed |
Email Sync
Every email connection is covered by four layers:
- Historical backfill (on connect) — when you first connect an account, Workestra asks how far back to pull: 30 days, 90 days, 12 months, or everything. The job runs in the background with a visible progress bar on the connection card and pause/resume/cancel controls.
- Real-time webhooks — Outlook pushes new messages within seconds via a Microsoft Graph subscription.
- Daily scheduled sync — a background job pulls any missed changes and renews webhook subscriptions before they expire (Graph subs expire after 3 days).
- Manual Sync Now button — on each connection row in Settings, forces an immediate delta sync and shows the result inline.
Where mail appears
Connected mail surfaces across the product:
- Sidebar → Inbox — the single destination for email AND activity notifications. Has a Compose button, per-account filter (when the Email tab is active), search, and the standard filter chips (All / Unread / Emails / Mentions / Assigned / per-module).
- CRM contact and deal pages — every thread with the counterparty in a right-rail panel. Auto-linked by address match.
- Support ticket pages — threads with the customer contact.
- Recruiting candidate pages — dedicated Email tab alongside Overview, Resume, Evaluation, etc.
Read and unread state syncs in both directions: marking a message read in Workestra also marks it read in Outlook (shared-mailbox team members will see the same state), and vice versa on the next sync.
Sync Behavior by Provider
| Feature | Gmail | Outlook |
|---|---|---|
| Initial Sync | Last 30 days | Last 30 days |
| Real-time updates | Periodic polling | Yes (Microsoft Graph webhooks) |
| Fallback sync | Daily cron | Daily cron |
| Manual Sync now | Yes | Yes |
| Two-way Read Status | Yes | Yes |
| Sent Items Sync | Yes | Yes |
| Attachment Sync | Metadata only | Metadata only |
| Multiple accounts | Yes | Yes |
| Shared mailboxes | No | Yes — see the guide |
Choosing a Send Method
When composing an email, the From selector lets you choose how to send:
| Method | Description |
|---|---|
| Connected Account (Gmail/Outlook) | Sends via your personal email account using the provider's API |
| Workspace Email | Sends via Resend using your workspace's configured sender identity |
Your last selection is remembered across sessions.
Managing Connections
View All Connections
Go to Settings > Integrations > Gmail or Settings > Integrations > Outlook to see every connected mailbox with a colored health badge:
| Badge | Meaning |
|---|---|
| Healthy (green) | Synced within the last 25 hours, no error |
| Never synced (blue) | Just connected, first sync in progress |
| Stale (amber) | No successful sync in over 25 hours — hit Sync now |
| Error (red) | Last sync failed; the message under the address explains why |
Each mailbox has its own Sync now button for on-demand refresh and a trash icon to disconnect.
Connecting multiple mailboxes from the same provider
You can connect more than one account from the same provider (e.g. personal + work Outlook):
- Connect the first account normally
- Click Add another account next to the existing connection
- The provider's account picker lets you pick a different identity
- Both accounts appear as separate rows with independent sync state
Microsoft 365 shared mailboxes (support@, sales@, …) are handled differently — they don't have their own password. See Shared Mailboxes.
Reconnect an errored account
If a connection shows an Error badge (typically "token expired"):
- Click the trash icon to remove it
- Click Connect again and complete the sign-in flow
Existing synced messages are preserved during reconnect.
Disconnecting
- Go to Settings > Integrations > Gmail or Outlook
- Click the trash icon next to the email account
- Confirm
What happens:
- Webhook subscriptions (if any) are deleted from the provider
- No new emails will sync
- Previously synced emails remain in Workestra
- If this was an Outlook connection that delegates to shared mailboxes, those shared mailboxes are disconnected too
- You can reconnect anytime
Troubleshooting
Common Issues
| Issue | Solution |
|---|---|
| "Connection failed" | Check internet, try incognito mode, clear cookies |
| "Token expired" | Click Reconnect and sign in again |
| "Permission denied" | Disconnect, remove app permissions, reconnect |
| "Admin consent required" | Contact your IT administrator |
| Emails not appearing | Check sync status, try manual sync |
Provider-Specific Help
- Gmail Troubleshooting � Google Account permissions
- Microsoft 365 Help � Detailed Outlook setup guide
Next Steps
- Microsoft 365 Integration — Deep dive into Outlook/Office 365 setup
- Shared Mailboxes — Connect support@, sales@ and other Microsoft 365 shared mailboxes
- Historical backfill — Pick a time range and pull existing mail
- Inbox — Unified destination for email + notifications, with Compose and per-account filter
- Email in your modules — How mail appears on contact, deal, ticket, and candidate pages
- Sending Emails — Compose emails with CC/BCC, signatures, and tracking
- Email Signatures — Create and manage signatures
- Workspace Email Settings — Configure Resend, domain verification, and rate limits
- Bounce Tracking — Monitor delivery status and bounces
- Scheduled Emails — Send emails at a future time