Most sales tax rules don’t make sense to the average person but there are some sales tax rules that don’t make sense to anyone, even a seasoned tax professional. Take candy. Candy has been moved by many states into the taxable category– but it’s not that simple. If you buy Twix in package of six in New York, it’s a nontaxable cookie. Buy a package of two, and it’s taxable candy. In both Kentucky and Missouri, candy with flour in it is not taxable. If you’re craving chocolate covered cherries, you’ll pay sales tax. But if you’ve got chocolate covered pretzels in your basket, you won’t. The reasoning behind it probably has to do with protecting wheat producers from reduced market share due to sales tax increasing the overall price of the product. But in any case, figuring out the rules and filing your sales and use tax can be pretty complicated when you take into account rules with such specific restraints.

On the other hand, Wisconsin taxes marshmallows unless they contain flour. Flour shows up in another weird sales tax rule. A sliced bagel in New York is considered taxable whereas a whole, unsliced bagel isn’t. The act of slicing the bagel makes the breakfast treat fall into the prepared foods category that’s taxable by New York standards. However, if the customer opts for a whole bagel, there’s no sales tax attached to the transaction. It’s not just flour. In Texas, cowboy boots are not taxable. Climbing boots are. Colorado taxes only inessential food packaging. That means you don’t collect taxes for the coffee you serve the cup in — but you do have to collect it for the lid you put on that cup. There are hundreds of other weird and wacky tax rules like this that can make filing difficult and time consuming. Share your favorites with us in the comments.