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I've noticed this too. Most of the time it works, but ever so often it fails.
I wonder if it could be a file size limit or something? Some screenshots will be more complex than others and thus might be just the wrong side of the line for uploading. I've not looked into in detail though, so can't say for sure.
Definitely not a size issue. Most of the time it's a meme I copied that is just a less jpegified version of one someone posted. It's not something I want to save to my phone and waste space, and it's too much effort to go back through and delete after I'm done than it's worth.
Here is a recent example
https://lemmy.world/comment/13317034
Yeah, it didn't seem all that likely to be the reason.