Digital gamification has been studied extensively in different contexts across information systems and digital marketing. Interestingly, scholarly studies in information systems/marketing regarding the benefits of digital gamification are mixed, with several research works reporting negative outcomes. Our study attempts to resolve these contradictions and explain why digital gamification failed in certain instances—the target customers were not ready. The present study, done in the USA covering 446 usable responses, adds to the extant literature in many ways. First, we throw light on gamified engagement programs and the mediating role of customer readiness and consequent outcomes. Our results reveal that simplicity and information quality are other important dimensions of gamified engagement programs, in addition to intrinsic and extrinsic game dynamics, for achieving adequate customer readiness. Additionally, customer participation makes the greatest contribution to company engagement, followed by program loyalty and program satisfaction. We conclude with the study’s implications on different fronts.