To understand how the software suite needed to scale for Major Theater Operations, we conducted extensive research combining contextual inquiry, observation, and collaborative workshops. Our team traveled to exercises and training drills to observe what large-scale operations looked like in practice, and we met with over 100 airmen—both current and prospective users—across multiple Air Operations Centers. By engaging with users in their day-to-day environments, we captured expectations, pain points, and key differences between routine workflows and combat-level demands. We mapped use cases, jobs-to-be-done, and identified gaps in system completeness for major combat operations. Alongside users and product stakeholders, we facilitated MoSCoW exercises to align business and user expectations. We also conducted comparative analyses between daily operations and large-scale combat operations, surfacing deviations and scalability challenges. To translate these findings into actionable insights, we created service blueprints, user maps, and process/service maps to explore workflow simplifications for the transitional application. This research provided the foundation for framing the core problem: ensuring the suite could evolve from supporting day-to-day planning into a tool resilient and intuitive enough to handle the scale and complexity of major theater operations.