How to check if emails from a user is getting hung up on our Exchange server

We have Exchange Server 2010 and I have had a user tell me that her emails to a particular customer all other emails either sent from her or received from other customers come in just fine.

We had the one customer send a test email to us and it came through however when we tried to reply from the exact same email they received nothing on their end.

Any suggestions would be great.
cmdolcetAsked:
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Guy LidbetterConnect With a Mentor Commented:
You will need to speak to your DNS provider to get the PTR records created.
A lot of companies are now using systems that require this.
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Guy LidbetterCommented:
Hi,

Run a get-messagetrackinglog for the time frame the mail was sent e.g.

Get-transportserver | get-messagtrackinglog -start "11/02/2015 09:00:00" -End "11/02/2015 09:10:00" -Recipients "Customer@email.com" | export-csv <CSVFile>

What you are looking for is a Source\EventID of SMTP\Send - This means it has left the building... and is an issue on your customer side.

If you are using a smart-host or service like messagelabs you can check the tracking logs on them too... otherwise check the Queue Viewer Tool in the Exchange Console and look for anything that's stuck there...
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AmitIT ArchitectCommented:
Create new message with option enable request a delivery report and read receipt. Then send message to user.
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cmdolcetAuthor Commented:
OK checking the Queue viewer tool I saw the emails that are listed in there. it says under the Last Error that 400 4.4.7 Message delayed. There are about 11 messages in there all to the same email end user.
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cmdolcetAuthor Commented:
It says that there Comcast requires that all mail servers must have a PTR record with a valid Reverse DNS entry, and that our mail servers does not. However we were able to send to them before.
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Manoj BojewarCommented:
Check Message tracking tool which shows delivery status of every mails sent and receive by server.
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cmdolcetAuthor Commented:
OK great I will start there. One more question.....Our ISP is AT&T would it be something on AT&T side or would it be something configurable on our Exchange server.

Thanks.
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Guy LidbetterCommented:
Wherever your external DNS MX Record is hosted, it's not an Exchange config. The PTR record needs to match whatever HELO\EHLO namespace your server provides.
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dsnegi_25decConnect With a Mentor Commented:
Yes ,  you have to ask AT&T  for create PTR record. they well create on there end.

From you will they will need your  domain name that's it.
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