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Unable to send some emails via Microsoft365 (Office365)
Posted by Sinclair Hughes on 05 March 2021 01:31 PM

On Tuesday this week Microsoft put out an urgent security bulletin  informing of a serious threat to Exchange Server.  Recent changes made to their Exchange Online (Office365) service has caused some emails not able to be sent from SPM or PHM if you are using the SMTP Relay option.  The error is likely to appear as “Authentication failed because the remote party has closed the transport stream”.

Emails can be sent through Office365 email servers using either:

  • Authenticated Client SMTP, or
  • SMTP Relay (using an Outlook connector)

In the new 409.6 release of SPM & PHM Incisive have made some changes to allow the SMTP Relay correctly communicate with Exchange Online.

If you are using 409.4 or earlier you will need to use the Authenticated Client SMTP option.  Your IT technician will need to be involved to configure the authentication settings.  

Authenticated SMTP requires authentication to be enabled at the Tenant and the Mailbox level.  
https://docs.microsoft.com/en-us/exchange/clients-and-mobile-in-exchange-online/authenticated-client-smtp-submission

In SPM/PHM, configure the options for each Provider in Setup > Provider > Email   (call Incisive for the Security code)

SMTP Server Settings

SMTP Server Name:    smtp.office365.com
SMTP Encryption:       TLS
SMTP Server Port:      587  (needs to be an open Outgoing port)

Account Authentication

SMTP Authentication required
Authentication Method:     AUTO or LOGIN
Account Username:          The email address of a user account
Account Password:           The password for the user account

Troubleshooting

  • Use the Check Connection and Send Test Email.
    Look at the log as it will explain the problem.  Scroll to the bottom of the log for the most recent entry.
  • Check port 587 is open  (Use Telnet if you are not sure)
  • Check that both the Tenant and the Mailbox user are authenticated in Microsoft365 Admin Centre.