Hello everyone! I'm hoping to get some expert help on an issue we are having.

we are moving from an on prem exchange server to O365, and our listserv is one of the last things we need to move off of the on prem relay.

i'm leveraging the following documents:

https://www.lsoft.com/news/techtipLSV-issue3-2015.asp

http://www.lsoft.com/resources/pdf/wp-UsingMSIISSMTP.pdf

https://docs.microsoft.com/en-us/Exchange/mail-flow-best-practices/how-to-set-up-a-multifunction-device-or-application-to-send-email-using-office-3?redirectSourcePath=%252farticle%252fHow-to-set-up-a-multifunction-device-or-application-to-send-email-using-Office-365-69f58e99-c550-4274-ad18-c805d654b4c4

and we are really struggling to get our emails to flow through o365. When we send an email, i see it flow through the IIS SMTP service, into the "Queue" folder, then it ends up in the "badmail" folder with the following error:

Action: failed
Status: 5.2.0
Diagnostic-Code: smtp;554 5.2.0 STOREDRV.Submission.Exception:SendAsDeniedException.MapiExceptionSendAsDenied; Failed to process message due to a permanent exception with message Cannot submit message

This implies to me that it is an issue with our connection to O365, but i can not determine where that error is. we did set it up per the first link, so with smtp.o365.com, port 587 and an authenticated mailbox. When i use that relay to "test" emails, sending as the authenticated user, mail flows, so i know the connector works.

Has anyone gone through this that may be able to shed some light on the situation? we'd prefer to use an authenticated connection to smtp.o365.com instead of relaying off of the protection link from the mx record, but maybe thats the only way, despite what the lsoft documentation states? Any assistance would be GREATLY appreciated in this.

Thank you everyone.

Michael

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