Offline Files Access Denied over VPN

I just tried taking a Windows 10 laptop on the road for the first time.  Everything was great until I tried the VPN for the first time.  Suddenly, I was getting Access Denied errors, and “You do not have permissions” errors for all files made available offline.  I confirmed the VPN tunnel and even browsed to other shared folders on the same server.  The offline files errors persisted after dropping the VPN.

When I returned to the domain Wi Fi, file synchronization completed normally and there were no errors at all.

Am I to believe that Windows 10 is completely incompatible with VPN synchronization?  I never had a problem with this on Windows XP, and I am dreading the months of research and experimentation normally involved in fixing this kind of Microsoft failure.

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Offline Files Stay Disconnected Over Wi-Fi

Configure Slow Link ModeEver since my move to a new apartment, I was frustrated by some of my network files going offline randomly and staying offline for 5 minutes or up to an hour or two.  The weirdest part was that it would only happen to the network files that were in a path with Offline Files enabled.  As a result, I would periodically lose access to files that were not marked “Always available offline”, and I would get frequent synchronization conflicts for any files that were still available offline.

Another symptom of this problem was that I could map a separate drive letter to the same or deeper path, not enable Offline Files for the networked drive, and then have no trouble with the files when I try to use the drive letter.  I could even browse shared folders using the server’s UNC path at the same time as my Offline Files cache seemed to be stuck offline.

I had several suspicions about why this was happening.  First of all, I had started using Wi-Fi networking on my desktop computer as a convenience until I could knock some holes in the apartment walls to run proper Ethernet cables.  The signal quality seemed good enough that I shouldn’t have persistent connection problems, yet the Offline Files system seemed central to the problem.  I eventually discovered that the Client Side Cache “slow link” mode was at fault for this whole mess.

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