When connecting your email to Freshsales, there may be instances when the email authentication does not go through and that you may have to troubleshoot the email connection to ensure that it is in order. Follow these steps to troubleshoot your email sync:
A. Check if you have opted for the right email client:
- If you are connecting a personal account, then please ensure that you have opted for Outlook. This includes for emails ending with outlook.com, hotmail.com, and live.com.
- If you are connecting a work email address like [email protected], then opt for Microsoft 365.
B. Check your IMAP and SMTP email permissions of your Mailbox
Please ensure that the following permissions are enabled before connecting your Microsoft 365 or Outlook Mailbox with Freshsales:
C. Check if your IT team mandates IP whitelisting of Freshworks IP
Freshworks IPs need to be whitelisted if your IT Team maintains a list of IPs to connect based on the region. Add IMAP IPs from Mail Service IP Details, Freshsales SMTP IP's
CUSTOM IMAP and Custom SMTP
CUSTOM IMAP and Custom SMTP
SYDNEY Region - CUSTOM IMAP and Custom SMTP
INDIA Region - CUSTOM IMAP and Custom SMTP
D. Check with your IT team for ssl certificates
Possible problem- There could be a mismatch between the Common Name(CN) in SSL certificates and the IMAP/SMTP server details entered in the form.
Here’s how you can solve this issue:
1. Verify the SSL certificate is valid with your IT team
2. Connect using the server name present in the SSL certificate
For example, if your CN on the SSL certificate is imap.domain.com, then IMAP server field must be imap.domain.com.
E. Check your Port numbers
1. Please make sure the port number entered in the form is open for accepting connections.
2. Check the SSL certificate for the exact port number of both SMTP and IMAP mailbox connections. 
General Port Numbers: