Despite more than half of India’s convict population serving the sentence of life imprisonment, there exists little critical writing or scholarly debate about this punishment. Following the decision by a constitution bench of the Supreme Court in 2015 in Union of India v. V. Sriharan & Ors., and the Criminal Law Amendment Acts of 2013 and 2018, life imprisonment has acquired a new-found texture of harshness which leaves little room for shortening of sentences otherwise provided for in law. This article begins problematising life imprisonment since it is expected that its use will be more rather than less frequent in view of these legal developments. Apart from discussing recent developments in life imprisonment, this article examines life imprisonment in a historical context, surveys the development of prisons in India and maps the mutation of the punishment of transportation into life imprisonment. The article claims that while life imprisonment existed alongside transportation, Indian prisons were not designed to house large numbers of life convicts. The transition from transportation to life imprisonment was unsupported by a robust legislative framework which necessitated a complex but unsatisfactory patchwork of judicial pronouncements and executive orders to overcome legislative lacunae. Such arrangements have made the punishment highly susceptible to arbitrariness. It is apprehended that increased reliance on life imprisonment may only serve to exacerbate existing problems of the criminal justice system, rather than finding sustainable solutions.