It is currently possible to upload e.g. five PDF documents at once into the Jedox Web Designer, by drag&drop'ing them on a folder.
However
this is not possible with .wss (and xlsx) files, and
if you already have PDF file(s) with similar name, then you get a prompt asking to replace file, but only for one of the files; the others are ignored
Allowing both would be helpful, especially when moving some contents.