Attachments in Apple Mail not received by addressee.  Same attachment sent via Google mail received ok.  Why?

I sometime need to send attachments such as pegs to a Uscg.mil address.  The attachments do not show up to the addressee, and it is probably due to a security firewall on the military side.  However, the same attachment goes through fine if sent using web mail (Gmail).  There must be some difference in the way Apple embeds an attachment that causes it to be rejected by the military security firewall.  Any thoughts on this?

Did you ever find a solution to your problem sending email with attachments? I am getting the same message  - "please select a different server" when I try to send emails with attachements...VERY FRUSTRATING...!

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