This paper explores the emergence of agile-inspired approaches in the critical infrastructure sector, with a focus on the current digital transformation of the Norwegian Oil & Gas industry. It addresses how traditional plan-driven development and strict architectural principles are challenged by the need to exploit the growing volume of operational data, in search for better, faster, and safer operations. We emphasize the increasing reliance on data for optimizing operations and the inherent risks and culture clashes between Information Technology (IT) and Operational Technology (OT). We furthermore discuss the role of cybersecurity in this transition, illustrating how increased connectivity and agile-like approaches can both mitigate and exacerbate security vulnerabilities.