ROROs, at first glance, appear to be stability nightmares with their relatively high vertical center gravity, relatively low metacentric height, and imposing freeboard. Their non-uniform cargo also causes concern in loading due to uncertainty in weights estimates and stowage locations. The Golden Ray is an example of a vessel design that was pushed to the limits of what is capable for ROROs, only to fail due to the complex nature of simultaneously meeting the loading criteria and keeping the vessel upright in a dynamic operating environment. Historically, naval architects have attempted to push the boundaries of what vessels are capable of by increasing size, speed, or maneuverability (and more), to carry more cargo or reach their destination quicker. They use the same criteria and programs that have served them in earlier iterations of the design, and have frequently overlooked the unpredictability of the marine environment and the domino effect that changing a single vessel characteristic can have on the rest of the design. This paper will discuss the stability of the Golden Ray leading up to its capsize in Brunswick, Georgia, and discuss other similar casualties where the boundaries of design were pushed but the full extent of failures that a vessel could encounter in its lifetime were not explored. The aim of this paper is to offer naval architects, computer program designers, and vessel operators teaching moments from past failures in vessel design and to offer risk mitigation strategies throughout the design and build process.