All steps :
I uploaded a pack of cards in .gif ( drop in )
When i do that got an error ( don't sreenshot it )
I realized that a card was missing ( the 'Ad' )
So i try to upload it again and this error occured ( again and again )
If i rename the image i can uploaded it ( like you can see in my screenshot )
Got another if i try to use the button "upload file" ( see this another screen )
I use uBlock Origin as Ad blocker. and I was able to recreate your problem.
If I disable the Ad blocker for the ai2.appinventor.mit.edu webpage uploading works again as expected!