Natural disasters such as earthquakes and hurricanes frequently strike Haiti and other Caribbean nations, leaving communities with damaged infrastructure and slow recovery processes. This paper explores how the integration of smart technologies can improve post-disaster engineering efforts. From drone-based aerial assessments to AI-driven planning tools, these innovations offer promising ways to accelerate damage evaluation, optimize logistics, and support safer rebuilding. Drawing on experiences from recent disaster responses in Haiti, this work presents a grounded perspective on both the potential and the challenges of implementing such tools in areas with limited resources and fragile digital systems. The aim is to highlight practical, context-sensitive approaches that can make engineering more resilient and responsive in uncertain global conditions. This study aligns with the IEOM 2025 theme by demonstrating how engineering and technology can come together to support vulnerable regions in a rapidly changing world.