Well on my failed attempt today I uploaded it from my photos, the same exact file i uploaded 6 days ago. Last week and today I uploaded, I uploaded it using Damus. So maybe Damus needs to update something in their image uploader?
Discussion
If it was identical file you would have gotten the old upload link. Since I suspect you downloaded the uploaded file, then it may gut have been different. We hash the original upload and match it to the hashes in our DB, and give you the old link if we have it 🐶🐾🫡
Well here's the same file from this morning, the one i shared in the iCloud link 
The hash is different, means that the file is not identical. Try uploading from Safari by going to https://nostr.build
Also, if you go to Photos and see the file and it doesn’t show animation, then it is not animated and will not work. GN 🐶🐾🫡🫂💤