1

I’m trying to set up email notifications in WSUS but I’m constantly getting the error mentioned in the screenshot.

System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [BN6PR11CA0037.namprd11.prod.outlook.com]
   at Microsoft.UpdateServices.Internal.BaseApi.SoapExceptionProcessor.DeserializeAndThrow(SoapException soapException)
   at Microsoft.UpdateServices.Internal.DatabaseAccess.AdminDataAccessProxy.SendTestEmail(String emailLanguage, String smtpUserName, String senderEmailAddress, String smtpHostName, Int32 smtpPort, String recipients)
   at Microsoft.UpdateServices.Internal.BaseApi.EmailNotificationConfiguration.SendTestEmail()
   at Microsoft.UpdateServices.UI.SnapIn.Dialogs.EmailNotificationSettingsDialog.backgroundWorker_DoWork(Object sender, DoWorkEventArgs e)

I sent a screenshot

Annotation_2019-05-02_125335.png
Annotation_2019-05-02_125335.png472×519 28.5 KB
of the current settings and I also followed the directions here: https://www.onlinenetworkssolution.com/2018/01/How-to-configure-email-notification-on-WSUS-Server.ht…

The SMTP relay has been set up and I’m pretty sure it’s a misconfiguration in there that is causing the issue.

Granted I am using Windows Server 2016, so I’m not sure if that makes a difference.

7 Spice ups
2

You are trying to send to O365, but the program doesn’t support TLS? For that you probably want to setup an SMTP relay on O365 and then put the correct SMTP information in. If you setup a relay, you do not use smtp.office365.com.

See this how-to for more information:

https://community.spiceworks.com/how_to/98692-create-an-smtp-relay-in-o365-to-allow-a-unitrends-appliance-or-other-device-to-send-email-without-tls

1 Spice up
3

+1 - No SSL/TLS setup available from WSUS.