Life imprisonment has been part of South Africa's penal regime for decades. This article analyses how this form of punishment has changed in meaning in since 1906. The author looks at life imprisonment during the death penalty period ; life imprisonment in the aftermath of the abolition of the death penalty ; life imprisonment under the Criminal Law Amendment Act, when it could only be imposed by the High Courts ; and life imprisonment during the Criminal Law Amendment Act, when the regional courts were also empowered to impose this sentence. The author discusses the laws and circumstances which prevailed in the above four periods. With life imprisonment now being the severest sentence that can be imposed in South Africa, the author highlights the challenges associated with it and calls upon the government, courts and civil society to think seriously about how this form of punishment should be administered so as to avoid confusing inmates and exposing the government to litigation.