In the effort to reduce frustration with the image uploading process, I do have a workaround with a so far 100% success rate. The bug seems to be related to uploading from your local hard drive. Using an image URL has yet to fail me. I have a dump folder on Imgur. If I need to upload an image to the forum, I drop it in that folder, click on it to get the direct URL (it's a button you can press), and use that instead of choosing a file. Yes, it's a tedious addition of several steps, but it does save time in the long run because it beats multiple click-waiting-failing cycles. I also have an extension for Chrome (and a different one for Firefox ) that will either send any online image to Imgur and fill your clipboard with the URL with a single right click, or allow you to do the same with a screen capture.