Older images and avatars not optimizing when rebuilding cache

I switched to optimized images and then rebuilt caches but then when I go to download the image or avatar to test it's still the original jpeg.

For an image attachment for AMS I had to delete and reupload the image for it to optimize. Rebuilding caches doesn't seem to be working. Should I open a ticket or is this user error?

I rebuilt caches many times after switching to optimized.

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