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In order for TLS to work, your server must have a certificate installed. You’ll see some valuable information about your configuration changes.

Check the Event LogĪs you are configuring the SMTP Server in IIS6, go to Event Viewer and filter the System log on Source smtpsvc. Update October 9, 2014: The Microsoft KB article has been removed, but the blog article is still there. It also has screen helpful shots to follow, not just text.

However that article was missing some key pieces of information.Ĭredit: This article pointed out the certificate requirement. I was following the smart-host method described in Microsoft KB2600912: How to set up an SMTP relay in Office 365. Yesterday I was trying to set up Office 365 to relay email messages from Line-of-Business applications.