Hello @spuder
Has this functionality changed at all?
The reboot resource used to be in the windows cookbook and was dealt with by a handler. There is now a reboot resource is core Chef with slightly different settings which can cause an immediate reboot.
The announcement for handling reboot between kitchen runs is Test-Kitchen 1.10.0 Released
I have a demo cookbook on my Github which appears to work with Chef 13.0.118 https://github.com/chrisgit/test_kitchen-multiboot
What is the new behaviour? Which version of ChefDK are you using?