Hi, same problem over here (in France) and it displays the same message "There was an upload problem, please try again". After spending quite a while on some French, UK and US forums, I have not found many highlights and I have not been able to resolve the problem. I have erased Messenger and re-uploaded and did the same for Voice Memos (dictaphone in France) and re-uploaded the Apps, then restarted my iPhone XR (Software version 13.4), and tried again...DOES NOT WORK! I have looked into all the possible settings for both Messenger and the Voice Memos Apps but could not trigger any option allowing a single voice memo transfer. I suppose that it is a glitch in the Messenger App latest version??? Anyone could help more or give a working solution? THANKS, Ben