I tried copying over a .zip file weighing around 5 GB from my Windows PC to the RPi using WinSCP, and usually when it reaches the 700 MB mark, it fails with this error:
Googled the error, most people who had the same error actually didn't have SSH enabled, but one thread I came across suggested removing the package, so I removed the openssh package, installed it again, reboted, this time the transfer got to around 1.2 GB in, and it failed again with the same error.
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Network error: Software caused connection abort Copying files to remote side failed
Tried transferring the file through VNC File transfer, significantly slower, but still fails less than halfway.
Screenshot of WinSCP: