Insightly Email Sync Not Working

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Ongoing Web Updated November 13, 2026Based on 2 user reportsHow we research

Quick answer

Insightly emails stop syncing when the Gmail or Microsoft 365 authorization expires or is blocked by an admin. Reconnect the mailbox first.

Most likely fix: Reconnect the mailbox

How to fix it

Try these in order — the most common fix is first.

  1. 1. Reconnect the mailbox

    1. Click your profile > User Settings
    2. Open the email/Gmail or Office 365 integration section
    3. Disconnect the account, then connect again and accept all permissions
    4. Send a test email to a known contact
    Did this fix it?
  2. 2. Check admin app access

    1. Ask your Google Workspace or Microsoft 365 admin to allow Insightly in third-party app access
    2. Confirm 2-step verification or conditional access is not blocking the sign-in
    Did this fix it?
  3. 3. Match the contact

    1. Make sure the email address exists on a contact record
    2. Move test emails to Inbox or Sent, not subfolders
    Did this fix it?

Symptoms

Sent or received emails no longer appear on contact or opportunity records.

Why it happens

  • Expired or revoked OAuth token (password change, security policy)
  • Admin restricts third-party app access
  • Emails are in subfolders or labels the sync does not read
  • Sender address is not on any contact record

This guide also covers

  • insightly email sync not working
  • insightly gmail sync
  • insightly office 365 email

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