Usually I don’t have that many issues with Windows 10, but somehow after last Windows update I lost control over the contents of the “Documents” folder which was being synced with a file server. I was able to add files but never delete them getting the error “Permission Denied”. Talked to the domain admin, he looked over the permissions on the file server and all seemed fine there. Reset the offline file sync cache, etc (the usual hints you get while googling resetting offline files sync issues) got me back permissions on my files, or so I thought.. After leaving the office I noticed in the evening that I have no more Documents at all. It turned out that after the reset Offline files were not syncing at all and I was able to access them only when I had connectivity to the file server. The issue was that offline files were in “sync pending state” and it wouldn’t actually start the sync.

Try the classics “reboot” the computer, no the sync would not start again, try resetting the offline files cache again – no success.. What actually worked for me was running:

gpupdate /force

After re-installing the group policy clicked on the sync offline files button and voila it synced like a charm again.