This chapter addresses the weaknesses of tax penalties in current law as deterrents of high-end tax noncompliance and describes how Congress could introduce tax penalties that vary depending upon taxpayers’ means. The chapter begins with a discussion of the possible motivations for individual tax compliance, including potential adverse consequences of noncompliance and, specifically, civil tax penalties. It then considers why current civil tax penalties often fail to deter high-end tax noncompliance. Finally, the chapter presents means-adjusted tax penalties as a new approach to the design of civil tax penalties, illustrates this approach with several examples, and addresses additional concerns.