Exchange relays to the SMTP server but the TO field in the email can’t be resolved by the SMTP serve

350300 pts.
Tags:
5.1.1 Error
Exchange Relay to SMTP Server
Exchange Server
IIS
Microsoft Outlook
SMTP server
I have Eroom running IIS smtp server in order for the app to receive mail. The problems seem to be: 1. Exchange relays to the SMTP server but the TO field in the email can't be resolved by the SMTP server because it will say From: Bob smith rather than Bsmith@maindomain.com 2. Outlook will put single quotes around the SMTP server's domain email address which will return a 5.1.1 error. It will be looking for 'it.test@eserver.domain.com' I found both of these by experimenting with the inetpub/drop folder on the Eserver. If I have just both the straight email addresses the mail will be delivered. Change one and it goes to BadMail. Is there a way for Exchange to relay it to the internal SMTP server with the To and From's just being email addresses?

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I think you need to capture the traffic using Wireshark or something. SMTP, whether it is Microsoft or not should not modify the TO field like you are saying. The Eroom server sounds like it is doing some kind of parsing or rewriting.

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