In some cases where SMTP AUTH commands are sent to the downstream mail server, Email security will fail if configured to use MTA mode and the recipient mailserver (Exchange) is not utilizing the option Manage Send as permission for the mailbox in question. In most cases, this will pertain to the outbound mailflow as rarely would SMTP Auth be enabled for inbound. With that being said, the caveat is not path specific and is a general consideration when facing SMTP AUTH and an Exchange facing recipient path.
Version Applicable: Â 8.3
This is a configuration issue with the downstream Microsoft Exchange server.

