Evacuation planning is a crucial component of national resilience in the context of increasingly complex emergencies, including armed conflict. Ukraine’s ongoing war has revealed critical infrastructure vulnerabilities and limitations of traditional evacuation strategies. This paper presents a transport-oriented evacuation framework, integrating Transport System Modeling (TSM) with scenario-based planning under real-world constraints. Four evacuation scenarios were developed: mass simultaneous (S1), staged with prioritization (S2), multimodal (S3), and intelligent ITS-based (S4). Based on operational data from Ukraine’s medical evacuations (2022–2023), the study evaluates mortality risk, network capacity, and system delays. Results show that scenarios S2 and S4 achieve the highest reduction in mortality (∆E ≈ 0.23–0.24) and improved operational performance, whereas S1 is prone to overload and excess mortality. The research emphasizes the role of digital tools, multimodal coordination, and real-time decision support in effective evacuation planning. Scenario-based modeling enhances system resilience, enabling preemptive risk mitigation. The proposed methodology is scalable and adaptable to various emergencies, aligning with the Sendai Framework and Sustainable Development Goals (SDGs).