Good news is I can reproduce what @gcliff is seeing using GitHub actions in openmrs-core 
https://github.com/openmrs/openmrs-core/pull/3380/checks#step:4:1935 Bad news is I did not fix the issue with my latest changes to the test 
Bright side is we can keep the tests disabled on master on Windows so devs on Windows can work. Meanwhile we can work on a branch like https://github.com/openmrs/openmrs-core/pull/3380 where we enable them, make changes and they will be tested on Windows 
Reproducibility is the first step 