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Once a file hasn't tweeted I've been unable to get it to tweet later by running the tweet step only (tweet2.py in my earlier screenshot). Maybe this means problem in the file? If the pi->phone hotspot or ssh connection is lost at any point could that cause it? It seems the only possible remaining explanation.
Fwiw: This is the one that didn't tweet yesterday I renamed it lake.mp4 once I'd scp'd it to the pi400 at home.
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rhb
cyclotron3k
There's 512mb file limit too, but I doubt you're hitting that.
I'd be retrying the failed files to see if it's an intermittent error (indicating and issue with the upload process) or constant (indicating an error with the file itself).