Palestinians in the Occupied Territories have been subject to increasing confinement, starting with prisons in the 1970s and 1980s and growing into a regime of checkpoints and walls that encircle entire towns and villages. After a historical review of the incremental stages of this incarceration, the article examines the overall impact of prisons, checkpoints, and walls, based on observations garnered from more than a dozen research trips over two decades and a review of research by others. Although these architectures are built and used in the name of security, findings show that mass imprisonment debilitates the Palestinian economy, forcing Palestinians to flee or resist. The final section compares the Israeli carceralization of the Occupied Territories to the US occupation of Iraq, suggesting that similar, albeit more violent, processes are underway.