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Another case where the upload was just randomly dying and continued after I've pressed "Next" several times.
TroperWall / WikiMagic Cleanup
Multiple times by now I have observed that the Image Uploader rejects an image, while the console types "Failed to load resource: the server responded with a status of 500 () 04:17:52.073 /ajax/uploadImg.php:1", the image gets submitted when I click Submit several more times.