I think what I do is similar to this URL, except I’m setting this up for SCCM and not IIS
http://community.spiceworks.com/attachments/post/0016/1638/configure-smtp-relay-for-office-365.pdf From: [email protected] [mailto:[email protected]] On Behalf Of James Avery Sent: Monday, March 23, 2015 3:30 PM To: [email protected] Subject: [mssms] SCCM 2012 R2 CU4 use Office 365 to send alerts via email Guys, I’m stuck on this and was wondering if anyone has configured SCCM 2012 R2 CU4 to send smtp email to office 365? The servers are cloud based. There are no on prem servers. I looked this over, and haven’t resolved anything. https://technet.microsoft.com/en-us/library/dn554323(v=exchg.150).aspx I keep receiving this error. ERROR: Connect to SMTP server has failure, detailed information are: 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~~ at System.Net.Mail.MailCommand.CheckResponse(SmtpStatusCode statusCode, String response)~~ at System.Net.Mail.SmtpTransport.SendMail(MailAddress sender, MailAddressCollection recipients, String deliveryNotify, SmtpFailedRecipientException& exception)~~ at System.Net.Mail.SmtpClient.Send(MailMessage message)~~ at Microsoft.ConfigurationManagement.NotificationManager.SmtpClientWrapper.SendEmail(MailMessage message)~~ at Microsoft.ConfigurationManagement.NotificationManager.SmtpServerTest.Test(Int32 siteNumber, AuthenticationMethod authType, String username, String encryptPassword, MailMessage message)
