This thesis considers how judges sentence. It explores and critically analyses judicial decision making in sentencing along with judicial perceptions of, and attitudes towards, the sentencing process. Building upon a thorough review of recent scholarship on judicial decision making and sentencing, and incorporating a comparative study of domestic and Commonwealth sentencing jurisprudence, the thesis comprises the first empirical study of judicial sentencing in Scotland in a decade. The thesis reports the results of an interview-based study with 25 serving Scottish judges. In particular it investigates judicial views on the importance of judicial discretion; the pursuit of individualised justice; the aims and purposes of sentencing; the role of personal mitigation, leniency and mercy; the use of guidelines, and whether consistency in sentencing is either achievable or desirable. The empirical findings reveal that, in order to comply with the demands of justice, the majority of Scottish judges consider the process of sentencing to be an adjudicative balancing of the relevant facts in every case – a delicate art based on competence, experience and expertise which is best achieved through a process of “instinctive synthesis”. This means that sentencing must remain an essentially discretionary process structured by appellate guidance. Through an integration of the concept of equity as particularised justice, the Aristotelian concept of phronesis (or “practical wisdom”) and appellate courts’ focus on the instinctive synthesis, the thesis argues that judicial sentencing methodology – to the extent that it relies on intuition and experience – is best viewed in terms of a phronetic synthesis of the relevant facts and circumstances of the individual case. The sentencing task is thus conceptualised as a form of case-orientated, concrete and intuitive decision making that seeks individualisation through judicial recognition of the profoundly contextualised nature of the process.