Pictures don't upload on first try

Was sending pictures over DMs and they wouldnt upload the first time. No message about failed upload/connection. They finish uploading and then nothing happens, the upload bars disappear and no pictures appear even after waiting a while.

Upon choosing the same images again and uploading them a second time they upload and send to other party. Other party confirmed that they did not receive duplicate of same images.

Happened a few weeks back for first time, thought of as simply connection issue. Idk about issues on pc, but this happened from my mobile phone.

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