SQL SERVER – Database Mail Error: The SMTP Server Requires a Secure Connection or the Client Was Not Authenticated. The Server Response Was: 5.5.1

I am an avid fan of Pinal Dave’s blog, it has been one of my go to blogs throughout my career as a SQL DBA. He has covered almost everything in the realm of SQL Server.

Recently when he blogged about a DB mail issue with this specific error message, I remembered facing a similar issue in one of our servers.

In our case a SQL Server job with SSIS Package designed to send mails to development team was failing with below error.

The SMTP Server Requires a Secure Connection or the Client Was Not Authenticated. The Server Response Was: 5.5.1

Server had multiple jobs using Database mail and only one was encountering this error. Digging deeper found out that while successful jobs had part of connection string as ‘EnableSSL= True’.

The job that was failing had connection string set as ‘EnableSSL = False’

Fixing the connection string fixed the job and it was running successful.

For more fixes related to this error message see Pinal’s blog posts

https://blog.sqlauthority.com/2018/06/30/sql-server-database-mail-error-the-smtp-server-requires-a-secure-connection-or-the-client-was-not-authenticated-the-server-response-sas-5-5-1/

https://blog.sqlauthority.com/2018/07/04/sql-server-database-mail-error-the-smtp-server-requires-a-secure-connection-or-the-client-was-not-authenticated-the-server-response-was-5-5-1-using-gmail/

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