It doesn't get much better than walking into a cell phone store ready to make an upgrade on a phone that you've had for years. You may know exactly what you want and can quickly answer every question the sales associate asks - except for one: Would you like to purchase the insurance for your phone? Instantly, you freeze in your tracks! You know you have a terrible track record with breaking your phone, dropping it in water, and all sorts of other incidents. But is it a good idea to pay extra every month just in case? Will you come out ahead, or end up spending more in the long run?