I've had a similar/same issue (although this is on Windows 7) with the Feb->Current monthly security rollups installing and rolling back ad nauseum. The reason I mention it is because dual-booting has been fingered as the cause in a few cases, whether or not that's grub or something else I'm not sure (no helpful error messages that I can find).
I'm personally about to drop the Windows partition completely, but if it's possible removing the dual-boot bit temporarily might help (although faffing around etc). Until the next time it happens! This happened a year or two back as well from memory.
I've had a similar/same issue (although this is on Windows 7) with the Feb->Current monthly security rollups installing and rolling back ad nauseum. The reason I mention it is because dual-booting has been fingered as the cause in a few cases, whether or not that's grub or something else I'm not sure (no helpful error messages that I can find).
I'm personally about to drop the Windows partition completely, but if it's possible removing the dual-boot bit temporarily might help (although faffing around etc). Until the next time it happens! This happened a year or two back as well from memory.