There are a lot of windows timeouts in the CI. The first one is spotted in March 4 2019, and since then there has been about one timeout a day across various tiers.

There are a few different cases that fails:

Build times out on Windows x64 - 49 times
open/test/jdk/:jdk_management times out - 34 times
open/test/jdk/:jdk_svc times out - 6 times
open/test/hotspot/jtreg/:hotspot_serviceability - 1 time

The build issue may be unrelated to the serviceability issues, but that would be a very interesting coincidence.