The booming growth of computational abilities in the 21st century has led to its assimilation and benefit in all horizons of engineering. For civil engineers, these advancements have led to groundbreaking technologies such as BIM, automation, and optimization. Unfortunately, even in an era of dwindling resources and dire need for sustainability, optimization has failed to attract implementation in practice. Despite an exponential growth as an area of research interest, the optimization of engineering structures such as reinforced concrete (RC) is still a complex task that requires multidisciplinary knowledge, hindering its practicability. Although past review papers have delved into this topic, they have only been able to cover the breadth of information available by covering broader aspects of optimization of structures. This study on the other hand aims to cover this topic in depth to uncover problem specific trends and issues, by focusing only on optimization of RC cantilever retaining walls. Although there is an abundance of research studies on this topic, there is an absence of any critical review to tie them up, and concurrently with its broader scope, it suffers the same lack of applicability in the field. The in-depth review presents a summarization of all the online publications including research articles, conference papers, and theses to the best of authors’ knowledge on the topic of RC cantilever retaining wall optimization. Geographical trends, regional developments, and prominent journals have been identified. The design codes, problem formulation, objectives, constraints, variables, and their optimization techniques are tabulated for ease of understanding. Unique areas of development investigated by the different researchers have been highlighted. Lastly, comprehensive recommendations for future works have been detailed with a focus on improving its applicability and assimilation into the construction industry.