That's a good question. The best answer is that the configuration needs to be a version controllable artifact just as much as your code is. Further, Windows Scheduler is known to drop jobs from time to time[1].

What was happening is that there was a job controller running on Linux that needed to contact the Windows machine and boot the job into action. One solution would have been to install a Jenkins slave instance, which turned out to be the solution eventually adopted.

[1] It's been a few years since I studied this, but it was a known issue in '08/09 or so.