When the master shuts down a daemon on Windows it invokes the configured target of WINDOWS_SOFTKILL which by default is condor_softkill. This exe basically looks for the Windows handle associated with a PID passed to it using the Win32 C API. When it finds a match, it "posts" a message of WM_CLOSE to that handle which is generally considered the graceful way of shutting down a Window console. Of course this works fine for the C++ exes like startd, kbdd, etc. which have handlers for WM_CLOSE provided by daemon core. In the case of the Python interpreter, WM_CLOSE is meaningless to it and application-specific. Not sure how the signal lib is implemented but SIGTERM certainly doesn't appear to equal WM_CLOSE.
One way to do this would be to use the Python Extensions for Windows. They can be used to properly register a Windows-specific handler for the WM_CLOSE message. However this adds additional dependencies we could do without.
Recommend an approach of just having:
1) a softkill replacement that touches a pid kill file on the local dir somewhere, and
2) update the configd to scan for this file on a timer
*** This bug has been marked as a duplicate of bug 586561 ***