In the IT landscape, DevOps is the preferred approach for developing and maintaining rapidly evolving systems that require continuous improvements. Yet, DevOps frameworks do not entirely prevent the accumulation of Technical Debt (TD), and under certain circumstances DevOps can even contribute to generating TD. This paper focuses on a specific type of TD, Entangled Technical Debt (ETD), that corresponds to the implicit complexification of a system’s design and the appearance of unintentional couplings in its architecture over time. Our work seeks to inform methods for Diagnosing and Locating ETD in DevOps frameworks. Through a research partnership with Ubisoft’s IT branch, an experimental case-study was conducted. It takes the form of an assessment of 6 innovative IT projects and a subsequent in-depth architecture analysis of an individual IT system, which enabled the characterization of the mechanisms linking DevOps to ETD. This allowed us to develop and test practical methods for diagnosing and locating ETD in IT systems.