Researchers investigating the psychological effects of choice have provided extensive empirical evidence that having choice comes with many advantages, including better performance, more motivation, and greater life satisfaction and disadvantages, such as avoidance of decisions and regret. When the decision task difficulty exceeds the natural cognitive resources of human mind, the possibility to choose becomes more a source of unhappiness and dissatisfaction than an opportunity for a greater well-being, a phenomenon referred to as choice overload. More recently, internal and external moderators that impact when choice overload occurs have been identified. This paper reviews seminal research on the advantages and disadvantages of choice and provides a systematic qualitative review of the research examining moderators of choice overload, laying out multiple critical paths forward for needed research in this area. We organize this literature review using two categories of moderators: the choice environment or context of the decision as well as the decision-maker characteristics.