Dropshare for iOS is currently designed to upload one file at a time.
We face a general usability issue here. All parts of Dropshare (also on the Mac) are designed to upload one file at a time - landing pages, URL copied to clipboard, all of this only works well with a single file. The Mac app however has either a queue (when trying to upload multiple files after another) or creates a zip archive with all files when a bunch of files are supposed to be uploaded at once.
We could migrate the later to iOS if this would help; when selecting multiple images from the gallery, Dropshare could archive them together into a single ZIP and upload this once instead.