Well I did a little more Trial & Error experimentation, and I've found that I get different behavior if I include <Python.h> before <boost/python.hpp> versus if I just omit <Python.h> inclusion all together. When I only include <boost/python.hpp>, I get an assertion instead of a crash. This assertion spits text out to my console window as follows: *Assertion failed: (op->_ob_prev == NULL) == (op->_ob_next == NULL), file ..\Objects\object.c, line 63* This assertion occurs during the call to Py_Initialize(). At this point this seems a little out of scope of boost (since at this point I haven't even called anything from boost that I'm aware of). I'm going to post this on the python mailing list to see if I can get some opinions there as well.