This is an open letter addressed to Chief Information Officers (CIOs). The presentation focuses on shadow AI, technical debt, and the security vulnerabilities they bring. By drawing parallels with IT practices of the past, the presentation explores the evolution of technology and technical debt. The goal is to show that the shadow deployment of generative AI within organizations, known as shadow AI, is familiar. We have seen it before, bringing security breaches and technical debt in its wake. “Dear CIO” is not just a warning but a guide to help organizations leverage the benefits of AI while protecting themselves from the risks that come with it.