Interest in retributive theory, and emphasis on proportionality between crime and punishment as a requirement of justice, revived in English-speaking countries in the 1970s. After less than a half century, however, retributivism’s influence is waning. It is beset by challenges. Some, such as difficulties in scaling crime seriousness and punishment severity, and linking them, are primarily analytical and of interest mostly to theorists. Others, such as trade-offs between proportionality and crime prevention, relate to real-world applications. Both sets of challenges can be explored in their own terms, and solutions can be sought. The bigger question, though, is whether the challenges are epiphenomenal and portend displacement of retribution as the most intellectually influential normative frame of reference for thinking about punishment. Only time will tell whether retributivism is in terminal decline. Most likely, the difficulties contemporary philosophers face are as much a reflection of a change in the zeitgeist, in prevailing sensibilities, in mentalités as of sudden realization that retributive ideas offer less guidance for thinking about punishment than was widely understood.