I am working with a customer for probably 2 months now trying to have similar issue fixed, except with AV. We totally gave up on content awareness, since we spent a month trying to figure it out, so working currently with senior T3 guy from Dallas TAC on av issue.
I find it super odd that even in my lab, which is on mgmt R82 and cluster R81.20 jumbo 99 , windows update keeps failing because of AV, but no matter what I bypass for ssl inspection, still does not work.
Once we do another remote with TAC, will update on results.
Andy
Best,
Andy