\nThis work on the proportionality of penalty jurisprudence in the criminal justice system revolves around the concept of sentencing of the convict. Through this work, the author tries to trace the systems of sentencing and penology prevalent from ancient Vedic and Medieval times in India, later the sentences during the British rule and prevalent practices in those eras. The conceptualization of sentencing has been elucidated in the later part, wherein, a broad and thorough idea of what sentence is and its value in the criminal justice system has been determined along with various facets and schools of sentencing. \n\nThis study is focused on offences under Section 21 of the Narcotic Drugs and Psychotropic Substances Act, 198S and the author, elaborates upon the various concepts and ingredients of this Section along with its tenets and attributes in sentencing of the offender convicted for this crime. The further part of this work, lists out cases on this Section under which the sentence was brought into picture by the Hon'ble Supreme Court of India and Hon'ble High Courts. Factors from these precedents have been elucidated which affect the sentence so afforded to the criminal. A tabulation of these factors on the basis of mitigating and aggravating circumstances has been provided which also depicts percentage of change in the sentence on the discovery of these factors in the facts of the case.