In the competitive world of retail, digital transformation is not just an option but a necessity to stay relevant and successful. One of the most emblematic examples of innovation in this field has been Amazon’s attempt to implement automated stores. These stores, designed to revolutionize the shopping experience by eliminating lines and improving efficiency, did not fully meet expectations. This whitepaper aims to explore what went wrong in this project and how we can learn from these mistakes to optimize our own digitization processes.