The concept of individualized Sentencing, as a core principle of modern criminal justice, aims to impose penalties that are proportionate and humane by considering each offender's psychological, social, and criminal background. Despite the existence of theoretical and Islamic jurisprudential foundations in Iran's legal system, the implementation of individualized Sentencing faces significant structural, legal, and procedural challenges. This article explores the legal obstacles and opportunities for individualized Sentencing in Iran, providing a multidimensional analysis rooted in theoretical, jurisprudential, and comparative frameworks. It begins by conceptualizing individualized Sentencing and outlining its reformative, reintegrative, and justice-driven objectives. The study then examines issues such as the lack of established judicial precedent, inconsistency with general criminal law principles, absence of professional assessment systems, and prevailing sociocultural pressures. The Islamic perspective is also evaluated, highlighting the potential support for individualized Sentencing through principles such as repentance, proportionality, and compassion. The comparative section of the paper reviews successful international models, particularly in addressing drug-related offenses. Furthermore, the article assesses the influence of human rights obligations and international criticism on Iran’s penal policies. In conclusion, it proposes legal reforms, structured offender assessment protocols, and professional training initiatives as strategic pathways to harmonize Iran's criminal justice system with the principles of individualized Sentencing.