Ok, so I dug into this today, and while I found a couple other glitches with the conversion process, the featured image stuff should be completely unaffected. What I found is that the featured image is simply stored as a post ID. I couldn’t find any instances in my database where the original filename was stored, except the GUID, which is not supposed to be changed. It’s stored as a url, but it isn’t supposed to be used as a url. Kind of weird, I know, and something that could affect a poorly written theme/plugin, but certainly not something that would affect WP core, as they never use that field to load the image.
I then tried to see if perhaps it was a permissions thing where the authors were uploading images that didn’t get optimized/converted, and then during editing perhaps it was being converted, but with background optimization, that simply isn’t feasible.
I even tried with background optimization disabled, like it would be if you were using the Shield plugin, and it takes a while longer, but it still seems to work just fine for me.
From what you said, the image only “disappears” on the post editor and the actual published post, so my suspicion is that something is referencing the GUID, that’s the only thing that would make sense to me at this point.
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