Ponies were very surprised when Jackpot Enterprises' managing director, Crystal Jackpot himself, started allowing Ponyville's richest residents to insure their properties with his company - not least because the last thing anypony ever expected was that Jackpot Enterprises would do something enterprising. However, they were even more surprised when a crippling blow was dealt the idea by none other than Princess Twilight Sparkle.
Not only did she not have her castle insured: she also urged every single one of her friends - her rich, powerful friends - not to take insurance out either. Nopony would suggest that Jackpot was a resentful stallion - nopony who didn't want to find himself homeless within the week, anyway - but it was, all the same, surprising for Twilight when just about everypony she knew took out insurance against, er, her.