Configuring SMTP Email Notification on WSUS server When using Outlook 365

Question

We have a SMTP relay set up on a different server. I have tried to set up email notifications from WSUS server. I get the following error when trying to test. We are using Outlook 365. I've tried using ports 25 and 587 respectively. Any ides? Thanks in advance!
System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.1 Client was not authenticated
   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)

Answer 1

We have a SMTP relay set up on a different server. I have tried to set up email notifications from WSUS server. I get the following error when trying to test. We are using Outlook 365. I've tried using ports 25 and 587 respectively. Any ides? Thanks in advance!
System.Net.Mail.SmtpException: The SMTP server requires a secure connection
You cannot email from a WSUS server direct to an O365 SMTP server, because the O365 SMTP Server *requires* a TLS-authenticated/encrypted connection and WSUS does not support TLS sessions. You'll need to have WSUS sent to an unencrypted onsite SMTP relay that
has the ability to initiate a TLS relay connection to O365.
Lawrence Garvin, M.S., MCSA, MCITP:EA, MCDBA
SolarWinds Head Geek
Microsoft MVP - Software Packaging, Deployment & Servicing (2005-2014)
My MVP Profile: http://mvp.microsoft.com/en-us/mvp/Lawrence%20R%20Garvin-32101
http://www.solarwinds.com/gotmicrosoft
The views expressed on this post are mine and do not necessarily reflect the views of SolarWinds.