The key to spending less money is to feel your spending when it happens. The reason EveryDollar doesn't automatically categorize your spending is to help you create an emotional connection with those transactions. We need to feel that money leaving our account. EveryDollar Plus is the closest thing to cash that has ever been built.
Plus, let's be honest, when you shop at Amazon or Target, can any software really guess accurately what you spent money on? Nope!