I made a site recently which needed to be security scanned by an external company using Web Inspect.
It failed... multiple times!
Actually the security guy said that Web Inspect was crashing. I had no idea why it was happening. Eventually I sat on the phone with the security guy and I started removing things from my master page.
It turns out that there was some combination of Javascript libraries that was causing Web Inspect to crash.
Lesson:
If you ever need to be security scanned and it crashes for an unknown reason, start stripping out js libraries.
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