2013, doing migration, can't reply to emails

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.

Hi,
From your description, I recommend you check the following things for troubleshooting:
1. When you reply an email, the subject contains "RE:". So please check if there is any transport rule prohibiting these replies. For example, reject emails if subject contains "RE".
2. Please take your time to collect the SMTP send logs and post them here for my further research. Here is the default location for your reference:
C:\Program Files\Microsoft\Exchange Server\V15\TransportRoles\Logs\FrontEnd\ProtocolLog\SmtpSend
Hope it helps.
Best regards,
Amy
Amy Wang
TechNet Community Support

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