Not WMP, but occasionally Windows Explorer crashes on me (it mainly seems to be connected with moving large numbers of photos around) and when I faithfully click the Send to MS box, it always gives the same useless advice. I've always assumed it to mean that they either haven't the faintest idea or, more likely, that they have no intention of wasting time and resources on my problem, but feel that they have to try to persuade me that they care.
Of course, I may be being overly cynical.