Narratives about Singapore’s prison often features success stories as told by the government’s Yellow Ribbon Project. What is often ignored is the abusive and de-humanising conditions that many of those who are imprisoned have to endure. In the last two decades, the Singapore Prison Service has re-branded itself as an institution which aims to “rehab, renew, restart”. Through first-hand accounts of those who have been incarcerated, this study takes a critical look at Singapore’s prison system and argues for decarceration, and an urgent need to uphold the rights of prisoners.