Outlook 2013, recipient not getting email attachments

This issue has become frustrating for me since I can't seem to find a solution...

One of my users is having issues sending email attachments to his customers.  It generally affects PDF files but sometimes JPGs and it's only a small number of customers that if affects, certainly not all.  We're using Outlook 2013 and this is a simple POP3 account.  He receives no bounce back message, just a response from the user on the other end saying they didn't get the attachments.  It's bizarre.  I've uninstalled, reinstalled, removed accounts, setup accounts, checked A/V, disabled A/V, checked our firewall, checked with our ISP and I can't find the smoking gun.  Has anyone ran across something similar here?  I'm at a loss.  

Thanks
trelectricAsked:
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David CarrCommented:
are the recipients internal or external to the sender?
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trelectricAuthor Commented:
All external.
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David CarrCommented:
It could be something on the receiver email system that is removing the attachments
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trelectricAuthor Commented:
We switched email hosting to Rackspace and haven't had an issue since.  Shame on the old provider for having issues, being blacklisted in places.
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