Why does Microsoft advertising generally suck?

Simple, they never focused on the real reason for advertising, to sell product. Microsoft has perfect opportunities to make some controversal ads. One would be saying MAC, I see you made it to the big league, how does that hacked iTunes app feel, sore? When you compare MAC OS it has some of the SAME EXACT authentication requests for permission Vista had, but Microsoft for whatever reasons seems to avoid hardball. If you want success, you have to be willing to step outside the comfort zone, or be able to make a unique pitch... Who can forget the anti-microsoft ads, nobody that watched them, I am sure.