I had an issue with an Exchange Edge server, the customer was sending PDF files compressed in ZIP or RAR files and they were bounced the email looks something like this:
RejectionResponse : Message rejected due to content restrictions or attachment restrictions.
I was puzzled in this one, because the engine configure to strip the content not to reject them and the attachment was not so harmful.
after little troubleshooting with get-attachmentfilterentry I didn't find anything that will block PDF or RAR or ZIP
so the solution was to disable the attachment filter engine remove-transportagent -identity attachment filter agent
Note: I am not sure about the identity thing so make sure that you type it correctly, to find our the exact name type get-trasnportagent
and I used Forefront to protect the environment pretty silly ha
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