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Emails with PDF attached to one domain get 4.4.7 QUEUE.Expired

When my users send email with a PDF attached to one domain they get an NDR (all other domains we send email with PDF attachments receive them fine). However email without PDF attachments goes through fine. I thought they must be blocking it on their end but they tell us that they are only having this problem with us. Any ideas on how to troubleshoot this?

Microsoft Exchange has been trying to deliver this message without success and has stopped trying. Please try sending this message again, or provide the following diagnostic text to your system administrator.

4.4.7 QUEUE.Expired; message expired ##

Thanks in advance for any advice :)
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mcwexchange
Asked:
mcwexchange
1 Solution
 
JamesSenior Cloud Infrastructure EngineerCommented:
Follow this link from Microsoft

http://support.microsoft.com/kb/818222/
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Rick FeeMessaging Engineer - Disaster Recovery EngineerCommented:
This problem is just with PDF attachements?   If you zip a PDF does it go thought without issue.   My guess is the problem is on their end with some type of anti-spam solution.   Do you know what they have as in anti-spam solution?
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mcwexchangeAuthor Commented:
Thanks EndureKona. I asked about their anti-spam filtering and found out that they have a really low limit on attachments they can receive. If the attachment size is too large they just drop the connection.
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