There is currently No Way to send a file from the Documents Tab in the Message Area. This is needed for many reasons but for an example: I have a Client who does Surveying. They Save the Map for the client in the Documents and that way all communication is there with any edits. They want to be able to either drag over from Documents Tab or Use The Attach File Option From The Menu as shown in the image. You can save from the messages area to documents but cannot go the other direction. Thank You!