||Despite the rentier state literature predicts a negative impact of the oil rent on the Middle Eastern monarchies, both Kuwait and Bahrain adopted constitutional experiments in the early twentieth century. Yet, Kuwait and Bahrain’s paths also both diverged. By employing a structured comparison of similar cases with different outcomes, this thesis seeks to explain the different paths pursued by the two monarchies, despite their identical liberalisation attempts. It is argued that the controlled parliamentary transition at the independence was planned by the rulers to secure their rule, while external threats acted as catalysts. While in Bahrain the external actors backed the Al Khalifa authoritarian tendencies, avoiding a parliamentary reinstatement, the Al Sabah repeatedly turned to the National Assembly to appease and balance the opposition. Consequently, a powerful parliament, considered dangerous in Bahrain, became an integral part of the Kuwaiti politics and identity.