Ok, this is the email leaving my server. I have changed the domains names for safety.
07:22 15:44 SMTPD(b74a0002261e16c7) >>> 220 mail.domainname.com (IMail 11.5 2886-1) NT-ESMTP Server X1
07:22 15:44 SMTPD(b74a0002261e16c7) [66.235.108.12:25] connect 174.141.12.138 port 53655
07:22 15:44 SMTPD(f6e00002261c0b3d) >>> 250 Message queued
07:22 15:44 SMTPD(f6e00002261c0b3d) [24.106.211.10] E:\Imail\Spool\Df6e00002261c0b3d.SMD 18481
07:22 15:44 SMTPD(b74a0002261e16c7) <<< EHLO SageAdmin
07:22 15:44 SMTPD(b74a0002261e16c7) [174.141.12.138] EHLO SageAdmin
07:22 15:44 SMTPD(b74a0002261e16c7) >>> 250-mail.domainname.com says hello
07:22 15:44 SMTPD(b74a0002261e16c7) 250-SIZE 0
07:22 15:44 SMTPD(b74a0002261e16c7) 250-8BITMIME
07:22 15:44 SMTPD(b74a0002261e16c7) 250-DSN
07:22 15:44 SMTPD(b74a0002261e16c7) 250-ETRN
07:22 15:44 SMTPD(b74a0002261e16c7) 250-AUTH LOGIN CRAM-MD5
07:22 15:44 SMTPD(b74a0002261e16c7) 250-AUTH LOGIN
07:22 15:44 SMTPD(b74a0002261e16c7) 250 AUTH=LOGIN
07:22 15:44 SMTPD(b74a0002261e16c7) <<< AUTH LOGIN
07:22 15:44 SMTPD(b74a0002261e16c7) >>> 334 VXNlcm5hbWU6
07:22 15:44 SMTPD(b74a0002261e16c7) >>> 334 UGFzc3dvcmQ6
07:22 15:44 SMTPD(b74a0002261e16c7) >>> 235 authenticated
07:22 15:44 SMTPD(b74a0002261e16c7) Authenticated
support@mail.domainname.com, session treated as local.
07:22 15:44 SMTPD(b74a0002261e16c7) Connection Check processing halted. Skip Spam set.
07:22 15:44 SMTPD(b74a0002261e16c7) <<< MAIL FROM: <
support@domainname.com>
07:22 15:44 SMTPD(b74a0002261e16c7) [174.141.12.138] MAIL FROM: <
support@domainname.com>
07:22 15:44 SMTPD(b74a0002261e16c7) >>> 250 ok
07:22 15:44 SMTPD(b74a0002261e16c7) <<< RCPT TO: <
brandon@mwesServerdomain.com>
07:22 15:44 SMTPD(b74a0002261e16c7) [174.141.12.138] RCPT TO: <
brandon@mwesServerdomain.com>
07:22 15:44 SMTPD(b74a0002261e16c7) [x] looking up mwesServerdomain.com in HOSTS
07:22 15:44 SMTPD(b74a0002261e16c7) >>> 250 ok its for <
brandon@mwesServerdomain.com>
07:22 15:44 SMTPD(b74a0002261e16c7) <<< DATA
07:22 15:44 SMTPD(b74a0002261e16c7) >>> 354 ok, send it; end with <CRLF>.<CRLF>
07:22 15:44 SMTPD(b74a0002261e16c7) >>> 250 Message queued
07:22 15:44 SMTPD(b74a0002261e16c7) [174.141.12.138] E:\Imail\Spool\Db74a0002261e16c7.SMD 17366
07:22 15:44 SMTP-(b74a0002261e16c7) processing E:\Imail\Spool\qb74a0002261e16c7.smd
07:22 15:44 SMTP-(b74a0002261e16c7) Authed User support@
07:22 15:44 SMTP-(b74a0002261e16c7) sender <
support@domainname.com>
07:22 15:44 SMTP-(b74a0002261e16c7) recip is <
brandon@mwesServerdomain.com>
07:22 15:44 SMTP-(b74a0002261e16c7) [x] looking up mwesServerdomain.com in HOSTS and MX
07:22 15:44 SMTP-(b74a0002261e16c7) [x] looking up mwesServerdomain.com in HOSTS and MX
07:22 15:44 SMTP-(b74a0002261e16c7) closed E:\Imail\Spool\_b74a0002261e16c7.~md - 1
07:22 15:44 SMTP-(b74a0002261e16c7) R<
brandon@mwesServerdomain.com> - 1
07:22 15:44 SMTP-(b74a0002261e16c7) [x] doing direct send mwesServerdomain.com
07:22 15:44 SMTP-(b74a0002261e16c7) Trying mwesServerdomain.com (0)
07:22 15:44 SMTP-(b74a0002261e16c7) Enumerating MX records for host mwesServerdomain.com
07:22 15:44 SMTP-(b74a0002261e16c7) Trying to connect to host 66.235.107.67
07:22 15:44 SMTP-(b74a0002261e16c7) Attempting to connect to host: 66.235.107.67
07:22 15:44 SMTP-(b74a0002261e16c7) Connecting socket to SMTP service on host <66.235.107.67> using tcp protocol.
07:22 15:44 SMTP-(b74a0002261e16c7) using source IP for mail.domainname.com [66.235.108.12]
07:22 15:44 SMTP-(b74a0002261e16c7) 220 fimail.domainname.com (IMail 11.5 34-1) NT-ESMTP Server X1 (MP)
07:22 15:44 SMTP-(b74a0002261e16c7) Verifying SSL settings for host 66.235.107.67
07:22 15:44 SMTP-(b74a0002261e16c7) >EHLO mail.domainname.com
07:22 15:44 SMTP-(b74a0002261e16c7) 250-fimail.domainname.com says hello
07:22 15:44 SMTP-(b74a0002261e16c7)
07:22 15:44 SMTP-(b74a0002261e16c7) >MAIL FROM:<
support@domainname.com>
07:22 15:44 SMTP-(b74a0002261e16c7) 250-SIZE 0
07:22 15:44 SMTP-(b74a0002261e16c7) 250-8BITMIME
07:22 15:44 SMTP-(b74a0002261e16c7) 250-DSN
07:22 15:44 SMTP-(b74a0002261e16c7) 250-ETRN
07:22 15:44 SMTP-(b74a0002261e16c7) 250-AUTH LOGIN
07:22 15:44 SMTP-(b74a0002261e16c7) 250 AUTH=LOGIN
07:22 15:44 SMTP-(b74a0002261e16c7) >RCPT To:<
brandon@mwesServerdomain.com>
07:22 15:44 SMTP-(b74a0002261e16c7) 250 ok
07:22 15:44 SMTP-(b74a0002261e16c7) >DATA
07:22 15:44 SMTP-(b74a0002261e16c7) 250 ok its for <
brandon@mwesServerdomain.com>
07:22 15:44 SMTP-(b74a0002261e16c7) Unexpected DATA response from the SMTP server on mwesServerdomain.com: 250 ok its for <
brandon@mwesServerdomain.com>
07:22 15:44 SMTP-(b74a0002261e16c7) SMTP_DELIV_FAILED
07:22 15:44 SMTP-(b74a0002261e16c7) >QUIT
07:22 15:44 SMTP-(b74a0002261e16c7) 354 Enter mail, end with "." on a line by itself
07:22 15:44 SMTP-(b74a0002261e16c7) [5836] closing socket (0)
07:22 15:44 SMTP-(b74a0002261e16c7) Creating message from Postmaster
07:22 15:44 SMTP-(b74a0002261e16c7) Delivery process now using new file: bf3000000c282b19
07:22 15:44 SMTP-(b74a0002261e16c7) finished E:\Imail\Spool\qb74a0002261e16c7.smd status=1
This is the message hitting the Imail server running MWES
07:22 15:44 SMTPD(375400000022002f) [66.235.96.34:26] connect 127.0.0.1 port 1330
07:22 15:44 SMTPD(375400000022002f) [127.0.0.1] EHLO mail.domainname.com
07:22 15:44 SMTPD(375400000022002f) Could not construct the HTTP query to the CTIPD Daemon. Reason: Unable to connect to the remote server
07:22 15:44 SMTPD(375400000022002f) Connection Check: IPReputation. Completed in 1.203125 seconds. Total elapsed for this session 1.203125 seconds.
07:22 15:44 SMTPD(375400000022002f) [127.0.0.1] MAIL FROM:<
support@domainname.com>
07:22 15:44 SMTPD(375400000022002f) [127.0.0.1] RCPT To:<
brandon@mwesServer.com>
07:22 15:44 SMTPD(375400000022002f) Processing QUIT
Does it seem like since both servers are running IMAIL it is trying to send the message a different way?