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Receiving of email delayed for some external clients (with attached log from frontend smtpReceive)

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Hey guys,

I have a very weird problem. One of our clients is having issues sending emails to us. I had him do a test, and I eventually received the email about 8 hours later.  I checked the SMTP front end log, and I saw two smtp events, they were both identical but only the second one went through. 

Now I have had him try resending again...I see his server contacting our server, and from what I see below I SHOULD have received an email but I did not.

Can anyone read this log to see what the hell is going on?

Here is the SMTP front end log:

2013-10-24T17:44:18.705Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,3,192.168.100.63:25,128.233.241.11:34229,<,EHLO barracuda.stmcollege.ca,
2013-10-24T17:44:18.705Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,4,192.168.100.63:25,128.233.241.11:34229,>,250-S8EX1.network.caedm.ca Hello [128.233.241.11],
2013-10-24T17:44:18.705Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,5,192.168.100.63:25,128.233.241.11:34229,>,250-SIZE 15728640,
2013-10-24T17:44:18.705Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,6,192.168.100.63:25,128.233.241.11:34229,>,250-PIPELINING,
2013-10-24T17:44:18.705Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,7,192.168.100.63:25,128.233.241.11:34229,>,250-DSN,
2013-10-24T17:44:18.705Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,8,192.168.100.63:25,128.233.241.11:34229,>,250-ENHANCEDSTATUSCODES,
2013-10-24T17:44:18.705Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,9,192.168.100.63:25,128.233.241.11:34229,>,250-STARTTLS,
2013-10-24T17:44:18.705Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,10,192.168.100.63:25,128.233.241.11:34229,>,250-X-ANONYMOUSTLS,
2013-10-24T17:44:18.705Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,11,192.168.100.63:25,128.233.241.11:34229,>,250-AUTH NTLM,
2013-10-24T17:44:18.705Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,12,192.168.100.63:25,128.233.241.11:34229,>,250-X-EXPS GSSAPI NTLM,
2013-10-24T17:44:18.705Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,13,192.168.100.63:25,128.233.241.11:34229,>,250-8BITMIME,
2013-10-24T17:44:18.705Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,14,192.168.100.63:25,128.233.241.11:34229,>,250-BINARYMIME,
2013-10-24T17:44:18.705Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,15,192.168.100.63:25,128.233.241.11:34229,>,250-CHUNKING,
2013-10-24T17:44:18.705Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,16,192.168.100.63:25,128.233.241.11:34229,>,250 XRDST,
2013-10-24T17:44:18.798Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,17,192.168.100.63:25,128.233.241.11:34229,<,MAIL FROM:<jmariano@stmcollege.ca> SIZE=45149,
2013-10-24T17:44:18.798Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,18,192.168.100.63:25,128.233.241.11:34229,*,08D094A16EB7E3FD;2013-10-24T17:44:18.627Z;1,receiving message
2013-10-24T17:44:18.798Z,S8EX1\Default Frontend S8EX1 (SMTP 25),08D094A16EB7E3FD,19,192.168.100.63:25,128.233.241.11:34229,<,RCPT TO:<jsmith@domain.ca>,

Thanks.

Edit: My Setup

2x Virtualized Servers running Server 2012 and Exchange 2013 CU2v2 (dual roles installed on both)


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