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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.
More info!
So, I tried to post this image from a copy/paste and it would not work: https://morejpeg.com/Image/View/09984d7c-579e-ef11-8104-ea49aec8cc27
But then I found this image from a twitter post and it worked. It lets me upload it to the same post, either in a new comment or editing the one I posted:
