Gamification is a strategy, methodology, or activity that has picked up pace over time and has been successfully deployed in organizations. Despite massive efforts to capture the success of the deployment of gamification in implementing innovation, its failure in this regard has hitherto been ignored. Until recently, it has been difficult to understand such failure from a contributing factor perspective. In bridging this gap, we conducted our study through the lens of problematization and social cognitive theory. We drew qualitative data from the field by recording the experiences and observations of stakeholders involved in attempting and failing to implement gamified projects in the retail industry. Our qualitative analysis was aimed at developing a signposting suited to help firms answer the fundamental question of “Why does gamification fail as an innovation strategy?” Our results highlighted four main factors that lead to the failure of gamified projects: a) self-efficacy, b) immersive dynamics, c) the personalization privacy paradox, and d) disengagement. Our study offers a conceptual framework suited to act as a guidebook for firms and consultants who wish to implement various gamified solutions at various stages. Further, we discuss the implications of our findings and propose future research perspectives