I sure wish it would. I never really understood the supposed psychology behind .99 and .95. To me, three nines looks less welcoming than three zeros.

It's so it doesn't cross the subconscious barrier of "under 20 dollars". $99.99 doesn't cross the subconscious barrier of $100 for example. It's probably been A/B tested to death, since it's so widespread among retailers.

Wow. I'd like to think people aren't wired like that, but I guess subconsciously there's lots of exploits like this.