Tax Law is especially interesting here, because you can basically depend on what the IRS has said but there's a chance that even if they said X, the tax court will actually rule Y (in your favor). Sometimes the risk can be worth it (if you made a good-faith effort to comply with a reasonable understanding of the law, and the court rules against you, you just have to pay the tax; even if you were found unreasonable you pay the tax + penalty which often isn't that much).