Every now and then when I add an image using drag and drop, it doesn't appear on the bottom of the box. What I do is click the "X" on the box to close it and then reopen the attachment manager and the image I added shows up a few seconds later. Just a small glitch. Closing and opening the attachment manager seems to work every time when it doesn't show up normally.
In Windows, if I have everything at full screen, I can click open the attachment manager, then click on the open folder where my photos are on the task bar at the bottom, select the photo I want to attach, then hover the mouse pointer over the browser icon on the task bar, which opens it up, then drop the photo in the attachment manager box. Having things at full screen helps find the photo among the bunches that I have.