Who This Is For / When to Use
Users who want to send and receive 1:1 emails from their personal Outlook inbox while keeping conversations logged in Kyrios.
Teams that need CRM visibility into email threads initiated from Kyrios.
Users who want Outlook email activity synced without exposing internal user-to-user emails.
What Outlook 2-Way Sync Does (Key Rules)
Syncs incoming and outgoing emails between Outlook and Kyrios.
Sync starts only after the first outbound email is sent from Kyrios.
Only threads initiated from Kyrios will continue syncing.
Emails will sync only if at least one recipient is a non-system user.
Attachments up to 25 MB are supported.
Sync stops immediately if the connection is disconnected.
Set Up Outlook 2-Way Email Sync
Step 1: Open Email Sync Settings
Go to Settings (bottom-left).
Select My Profile.
Open Email (2-way sync).
Select Outlook.
Click Connect.
Step 2: Sign In to Microsoft
Enter your Outlook email address.
Complete Microsoft authentication.
Step 3: Grant Required Permissions
Approve access when prompted. Kyrios (via LeadConnector) requires permission to:
Read and write your mail
Send mail as you
Read your profile
Read and write mailbox settings
Maintain access you have granted
Click Yes to continue.
Step 4: Confirm Connection
After authorization, your Outlook email will show as Connected.
You can use Update to switch to a different Outlook email without disconnecting.
Required First Action (Very Important)
To activate syncing:
You must send the first email from Kyrios Systems to a contact.
Threads started from your Outlook inbox will not sync.
Once initiated:
Replies from Outlook will sync into Kyrios.
Replies from Kyrios will sync into Outlook.
How Email Sending Works After Sync
Individual Emails
Sent from the user’s connected Outlook email address.
Outlook email becomes the sending domain.
Bulk Emails
If the From field matches the connected Outlook email → Outlook is the sender.
If the From field is empty or different → account-level email provider is used.
Workflows & Automations
Always send from the account-level email provider.
Personal Outlook email is not used for automation sends.
Privacy Behavior (Important Change)
Emails between Kyrios system users do not sync, even if they are contacts.
Sync occurs only when at least one external (non-user) contact is included.
This prevents internal or personal emails from being visible to admins or other users.
Attachment Support
Incoming and outgoing attachments up to 25 MB are supported.
Emails with attachments larger than 25 MB will not sync.
Common Issues and Fixes
Emails Not Syncing
Cause: First email was sent from Outlook, not Kyrios.
Fix: Send a new outbound email from Kyrios to the contact.
Thread Stopped Syncing
Cause: Sync was disconnected.
Fix: Reconnect Outlook and re-initiate the thread from Kyrios.
Attachments Missing
Cause: Attachment exceeded size limits or was sent before fixes.
Fix: Ensure attachments are ≤25 MB and resend if needed.
FAQs
What happens if I disconnect Outlook sync?
Syncing stops immediately. Existing and new threads will no longer sync.
Can I change my connected Outlook email?
Yes. Use Update Email under Email (2-way sync) without disconnecting.
Will emails started from Outlook ever sync?
No. Only threads initiated from Kyrios will sync.
Do bulk or workflow emails use Outlook?
No. Only manual 1:1 emails use the personal Outlook connection.
Are internal emails between users synced?
No. Emails between Kyrios system users are excluded for privacy.