Just a follow up, it looks like the randomization window on these machines is too large (+/- 4 Hours). These are non persistent VDIs and are only online for ~ 1 hour or so, so many of them are still on the definitions of the Parent VM, and don't update before logging off and "evaporating".
Since these are VDI we are nervous about changing the randomization window (2000+ virtual machines in scope). I'll let you know what this looks like when we down size the window to +/- 30 Minutes in testing. Hopefully clients get up to date a lot faster, even if they are non persistent and will "evaporate" after shutdown.