After sixteen months inside Cenovus, the problem became clear fast. Data did not fail because of tools, but because it fractured as it moved across the value chain. To understand where decisions actually break, this project followed data from upstream planning through midstream market analytics and into downstream commercial execution. Through interviews with professionals across Cenovus and Plains Midstream, the analysis traced how assumptions are created, transformed, and ultimately exposed to financial consequences. The findings showed that upstream feels data failures first, midstream trades speed over perfection, and downstream absorbs every error in P&L. The conclusion was blunt. Digital transformation in energy is not a technical challenge. It is a change management problem, where alignment, trust, and ownership matter more than dashboards or systems.