TheAnalogThing:Commonist

If you have lot's of images or some challenging (probably very large) files or images, you might be interested in a bulk image uploader tool.

Such a tool with a graphical user interface is Commonist. It is available at https://djini.de/commonist/ (but see also https://commons.wikimedia.org/wiki/Commons:Commonist). In order to have it play nice with this wiki, you have to choose the download version (ZIP or JAR) and setup the wikis.txt at your computer with some content like

me@localhost ~/.commonist % cat wikis.txt 
that _ https://the-analog-thing.org/w/api.php

You then just enter your user credentials and start mass uploading.