and it gave me that the upload was a duplicate, I'm not sure what's going on. I'm uploading these the same way I've been uploading from twitter all this time
Have you uploaded from a tweet with multiple images before? In those cases I've had to Open Image in New Tab for each one, use that as a source during the upload process, then go back and change the source to the parent tweet after it's been uploaded.
and it gave me that the upload was a duplicate, I'm not sure what's going on. I'm uploading these the same way I've been uploading from twitter all this time
Use topic #14156 for corrupted uploads like the above. Although it didn't actually make it to the image server, everything else, including the MD5 and filesize were set correctly, which is why it's detecting it as a duplicate.