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Finally, I managed to upload an animated GIF so it actually stayed animated!
Whenever I uploaded the GIF the animation stopped. I tried the upload via link, or from my computer and I was starting to get desperate. I was already thinking to make the entry as a Text Post and embed the GIF as an html <img>. But those show up as ugly little boxes on the dash and I hate them.
Some googling revealed that Tumblr converts oversized GIFs to JPGs which of course breaks the animation. JPEGs don’t support transparency and animation, only GIFs do. Taking a closer look revealed that this is exactly what happened to my GIF. It did show up as xxx.gif, but was in fact a JPEG that happened to have the filename .gif.
Great. So what is oversized? Somewhere I read that the limit is 500KB and GIFs larger then 500KB will be converted. But mine was only 252KB! Apparently it has to do with the width: my original image was 500px wide. When I downscaled it to 400px it magically started working. Wohooo!