Report Can't sync large files in Sync Troubleshooting Posted November 28, 2018 Update: I switched over from a Win7 32-bit virtual machine to a Win7 64-bit virtual machine, and now everything works fine. As near as I can tell everything was identical other than 32-bit vs. 64-bit (even the same file system; both were writing to an NTFS-formatted NAS). So my conjecture is that there is a 4GB file size limit with the 32-bit Windows client. I Googled this a fair bit and couldn't find this documented anywhere (on the contrary, I found plenty of references saying that there is no file size limit). If this is a known limitation, it would be good to document it better. If not, perhaps there is a bug in the 32-bit code.