The topic of “comfort letters” is forever an ongoing debate in Australia. There are arguments for and against enforceability of comfort letters, yet little has been said about how the “law” can be reformed. In support of enforceability, this article provides a comparative perspective on the American and Australian models and suggests that certain principles from the former could be adopted in Australia to eliminate the inconsistency in the treatment of comfort letter cases. The article also analyses Gate Gourmet and Lasalle Bank, two recent cases from Australia and the United States, respectively.