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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

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

July 4, 2018
Pinal Dave
SQL Tips and Tricks
Database Mail, SQL Error Messages, SQL Server Security

In my earlier blog, we saw one possible cause database mail error due to SSL settings. Today we will learn about another Database Mail Error. 

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SMTP setup error dialog.

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

June 30, 2018
Pinal Dave
SQL Tips and Tricks
Database Mail, SQL Error Messages, SQL Server

Database Mail with Gmail failed: the SMTP server requires a secure connection or the client was not authenticated, 5.5.1. Here is how to fix it.

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Man in glasses wearing black SQL Authority shirt.

SQL Authority News – Brent Ozar Unlimited Office Hours 2018/4/4 – Fun Experience

April 11, 2018
Pinal Dave
SQLAuthority News
Brent Ozar, Clustered Index, Database Mail, SQL Index, SQL Performance, SQL Replication, SQL Training

I joined Brent, Richie and Tara for Brent Ozar Unlimited office hours and answered live questions, from replication latency to disk space. Here is the list.

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SQL Server sysmail_configuration table.

SQL SERVER – sp_readrequest – Long Running Process

March 20, 2017
Pinal Dave
SQL Performance
Database Mail, SQL Scripts, SQL Server, System Object

sp_readrequest kept showing up as a long running procedure. It is Database Mail waiting on its queue with a 600 second timeout, usually nothing to worry about.

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Script level upgrade failed.

SQL SERVER – Script level upgrade for database ‘master’ failed – There is already an object named ‘DatabaseMailUserRole’ in the database

January 23, 2017
Pinal Dave
SQL Tips and Tricks
Database Mail, SQL Error Messages, SQL Scripts, SQL Server, Starting SQL

After patching, script level Upgrade for master failed: there is already an object named ‘DatabaseMailUserRole’. Here is what caused it and how to fix it.

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SQL SERVER - Stop Growing MSDB Database by Removing sysmail_mailitems History

SQL SERVER – Stop Growing MSDB Database by Removing sysmail_mailitems History

November 25, 2016
Pinal Dave
SQL Tips and Tricks
Database Mail, SQL Scripts, SQL Server, System Database

A client’s MSDB database had grown huge from Database Mail history and was slowing things down. Here is how to clean up sysmail_mailitems and stop the growth.

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Warning email icon.

SQL SERVER – Database Mail Breaks with TLS 1.0 Disabled Discovery – Notes from the Field #128

June 16, 2016
Pinal Dave
SQL Tips and Tricks
Database Mail, Notes from the Field, SQL Error Messages

Ryan Adams sent a test email and it never arrived. He explains why Database Mail breaks when TLS 1.0 is disabled and how he tracked down the cause.

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