This chapter addresses the role of tax advice in encouraging aggressive and abusive tax planning by high-end taxpayers. It begins with a discussion of the different roles of tax advice, one of which is its use as a form of tax penalty insurance. The chapter then shows how the rich benefit disproportionately from the ability to avoid penalties through tax advice. After describing these effects, we offer a proposal for incorporating means adjustments into the tax penalty defense rules, focusing specifically on tax advice, and we respond to potential objections and concerns.