a CMD-C and CMD-P forces not only the copy but the original to upload A name change will force the file to upload adding a tag to the file will force it to upload, etc.) I also noticed that if I use a python script to place a file in the folder, or I use the command line MV command to place a file in this folder - the problem does not occur and the file uploads fine. To work around problem, I noticed that any edit (to the file that fails to upload) will solve the problem. the latest update before the problem started occurring was MacOS 11.4. Prior to Big Sur these files would immediately begin synching to iCloud the second that they were created by the scanner software. Instead it is one linked to my Fujitsu scanner that is setup to automatically deposit pdf files into this folder once they are scanned. That said, one thing different for me from others in this forum reporting this problem is that the only folder this is occurring on with me is not one synced to Git. Prior to Big Sur I did not notice this behaviour. I have also noticed this behaviour since upgrading my 2015 MBP to Big Sur.