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Client not Authenticated error when exporting to Office365 on TLS port 587


QAID # 19416 Published

Question / Problem:

I am using the Export Connector EMail 1.0 and have configured to export to an Office 365 server using SMTP on port 587, which is the TLS (Transport Layer Security) port.

During Export, I receive the following error message:

The SMTP server requires a secure connection or the client was not authenticated. The
server response was: 5.7.1 Client was not authenticated.

Answer / Solution:

The cause of this issue can be that the email system doesn’t have the TLS(Transport Layer Security) encryption for SMTP (Simple Mail Transfer Protocol).

Since Office 365 Exchange Online requires TLS encryption of SMTP, your email system requires this feature for sending emails.

Here is an article that outlines how to configure Office365 for TLS:

How to Allow a Multi-function Device or Application to Send E-mail through Office 365 Using SMTP.

If you are configuring the Export Connector to use default credentials, then it could be that you have encountered the issue outlined in this article:

Smtp TLS authentication UseDefaultCredentials bug, using Office365 server as smart host

Applies to: 

Product Version
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