KB2574819 (DTLS) must be installed before KB2592687 (RDP 8.0), maybe the error was because you have inversed the order, or maybe because a reboot is necessary between the two installations. About a year ago, when the updates were released, I and others also had the problem of the installer running too early when we tried to integrate both, but I never encountered again with KB2574819 integrated and KB2592687 installed at RunOnce (always installed after VC++ Runtimes BTW). If you install only requested updates (GDR), there is five (four for x86) updates who must be installed at RunOnce: - KB931125 (rootsupd.exe) - KB976002 - KB2533552 - KB2592687 - KB2603229 (x64 only) You can see this topic for GDR only packs. I believe there is more if you use McRip repository. KB2574819-v2 is out by the way.