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Email fails to be sent or received when Server-Side Synchronization is configured with Gmail

Symptoms
If Microsoft Dynamics CRM is configured to use Server-Side Synchronization with Gmail, you may encounter one of the following errors:
  • Email cannot be received for the mailbox <Mailbox Name>. Make sure that the credentials specified in the mailbox are correct and have sufficient permissions for receiving email. Then, enable the mailbox for email processing.
  • An unknown error occurred while sending the email message "Test Message". Mailbox <Mailbox Name> didn't synchronize. The owner of the associated email server profile <Email Server Profile Name> has been notified.

Cause
This can occur for one of the following reasons:

Cause 1: The email address, username, or password in the mailbox record in Microsoft Dynamics CRM are not correct.

Cause 2: The correct port is not configured within the Email Server Profile record in Microsoft Dynamics CRM.

Cause 3: POP is not enabled on your Gmail mailbox.

Cause 4: A setting in Gmail is preventing Server-Side Sync from authenticating to the Gmail mailbox.

Resolution
Resolution 1: Verify the values of the Email Address, Username, and Password fields in the mailbox record in Microsoft Dynamics CRM.

Resolution 2: Open the Email Server Profile and then click Advanced. Set the Incoming Port to 995 and the Outgoing Port to 587.

Resolution 3: Follow the Gmail instructions for enabling POP:

Enable POP in Gmail

Resolution 4: Check your Gmail mailbox for an email regarding a blocked sign-in attempt. The message will include steps for how to unblock access. After following the steps, try testing and enabling the mailbox in CRM again. 

If the issue still occurs, refer to the following Gmail article which includes additional steps that may be necessary to enable email access from an app:

Troubleshoot sign-in problems

More information
The details section of the Alert may include the following text:

"Error : System.Net.Mail.SmtpException: Syntax error, command unrecognized. The server response was: 
   at System.Net.Mail.SmtpConnection.ConnectAndHandshakeAsyncResult.End(IAsyncResult result)
   at System.Net.Mail.SmtpClient.ConnectCallback(IAsyncResult result)"
Note This is a "FAST PUBLISH" article created directly from within the Microsoft support organization. The information contained herein is provided as-is in response to emerging issues. As a result of the speed in making it available, the materials may include typographical errors and may be revised at any time without notice. See Terms of Use for other considerations.
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Article ID: 3185281 - Last Review: 08/10/2016 01:34:00 - Revision: 1.0

Microsoft Dynamics CRM 2013, Microsoft Dynamics CRM 2015, Microsoft Dynamics CRM 2016, Microsoft Dynamics CRM 2016 Service Pack 1

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