We're starting a fresh 2013 install migrating from pop/smpt. I'm using the POP server as a smart host relay, so far there are 5 users in Exchange. The pop/smtp host forwards email to our domain into exchange and that works fine. So here's what's working and what's not
Inbound : works fine
Outbound using a company domain or internet domain email address : works fine
Outbound reply to an internet domain : doesn't work
It's weird. If i send an email from my gmail account to my exchange account, i get it. If i send an email from my exchange account to my gmail account, it works fine. But if i REPLY to my gmail account from my exchange account, the email gets lost somewhere.
If i use the mail flow diagnostic, I get this as the only hit as to what's going on:
Delivery Report for [company email address]
Submitted
4/17/2014 9:41 AM HQEXMB
The message was submitted to [server]
Pending
4/17/2014 9:41 AM [server]
Message was received by [server] from [server].
4/17/2014 9:41 AM [server]
The message has been queued on server [server]
since 4/17/2014 9:41:06 AM (UTC-08:00) Pacific Time (US & Canada).
The last attempt to send the message was at 4/17/2014 9:53:48 AM (UTC-08:00) Pacific Time (US & Canada)
and generated the error '[{LRT=};{LED=};{FQDN=};{IP=}]'.
Any ideas what's going on? I don't understand how I can send out a new email to an external mailbox but not a reply, that's a head scratcher.