It is NOT possible to upload a document to the contacts DOCUMENT section and then SEND that Document to the Contact. This is Very Important to have this function. Example ( Land Survey Company Attaches the Survey Document to THAT Contact, When the client pays their invoice then The Land Survey Company will Open That Contact and Drag That Document Over to the message area to send to the now finished client project.) This keeps the documents in the contact documents area for records or resend, and makes it very convenient to drag or even copy paste over to the message with that client. Thank You For Your Hard Work!