@chaley: The restart logic is in gui2/main.py around line 394 you can stick some print statements in there to see what is happening. (You will need to print to a file somewhere, as stdout/stderr are redirected to NUL).
print >>open('c:/log.txt', 'a'), 'some debug stuff'
or
from calibre import prints
prints('some debug stuff', file=open('c:/log.txt', 'a'))
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