Railway network upgrade programs are critical to meeting growing transportation needs but are far more complex than building new subway or LRT systems, as they must integrate new infrastructure into active rail operations with minimal disruption. These programs require coordination among multiple stakeholders and must contend with aging tracks, stations, and signaling systems. With more than 100 projects often running simultaneously and budgets ranging from millions to billions, each with its own delivery model, overall program management becomes highly challenging. This presentation examines these complexities, highlights what makes active‑network upgrades uniquely difficult, and outlines systemic issues identified through lessons learned.