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"Smtp server returned 530 MustIssueStartTlsFirst exception" occurs when using Server-Side Synchronization


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Symptoms

When you test and enable a mailbox in Dynamics 365 (formerly known as Dynamics CRM Online), you encounter one of the following errors in the Alerts area:

  • The email message "Test Message" cannot be sent because an error occurred while establishing a secure connection to the email server. Mailbox <Mailbox Name> didn't synchronize. The owner of the email server profile <Email Server Profile Name> has been notified.

    Email Server Error Code: Smtp server returned 530 MustIssueStartTlsFirst exception.

    ActivityId: <GUID>
    >Error : System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.5.1 Authentication Required. Learn more at
       at System.Net.Mail.SendMailAsyncResult.End(IAsyncResult result)
       at System.Net.Mail.SmtpTransport.EndSendMail(IAsyncResult result)
       at System.Net.Mail.SmtpClient.SendMailCallback(IAsyncResult result)
  • 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.
  • 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.


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Cause

This error can occur if you are using a POP3/SMTP email server profile and one of the following issues exist:

  1. The user name or password are not correct.
  2. If you are using Gmail, the option to allow less secure apps is disabled.


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Resolution

  1. Verify the User Name and Password values on the mailbox record in Dynamics 365 are correct. The error includes a link to the mailbox record in Dynamics 365.
  2. If you are using Gmail, verify the "Allow less secure apps" option is enabled:
    https://support.google.com/accounts/answer/6010255
 After changing any of the settings mentioned above, click Test and Enable on the mailbox record again.

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Article Info
Article ID : 3214706
Revision : 1
Created on : 1/7/2017
Published on : 12/21/2016
Exists online : False
Views : 313