It is at the court stage of criminal sentencing where justice is seen to be done. In this chapter, we discuss the sentencing of offenders who have committed more than one offense (i.e., what we call “multiple-offense” [MO] cases). We argue that efforts to develop sentencing policy and guidelines to support sentencers perform the cognitive task of sentencing MO cases may inadvertently undermine the search for justice. Specifically, we first emphasize the cognitive complexity of the sentencing task. We next present the approaches that different jurisdictions have adopted to sentencing MO cases, highlighting their implications for justice. Following this, we review the small body of past research on the approach taken in England and Wales (as well as several other common law countries) where MO cases are sentenced in their “totality”. Next, the chapter presents new empirical findings from our analyses of judgments made by the Criminal Court of Appeal in this jurisdiction. Finally, we recommend an empirical evidence-based approach to developing sentencing policy and practice in MO cases, pointing to avenues for future research in this regard, and identifying potential ways in which sentencers can be supported in the search for justice when sentencing MO cases.