Climate change is expected to alter the balance between heating, cooling, and natural ventilation in buildings, challenging design strategies developed under current climatic conditions. Courtyard buildings are sensitive to these changes because their performance depends on interactions between solar exposure, airflow patterns, and the thermal behavior of semi-enclosed spaces. Despite their widespread use, limited research has examined how courtyard configurations should evolve to maintain performance under future climate scenarios. This study investigates the climate resilience of a naturally ventilated courtyard office building through simulation-based evaluation of courtyard enclosure strategies. A multizone office building in Boston, Massachusetts, was developed using Rhino, Grasshopper, Ladybug Tools, and EnergyPlus. The baseline design incorporated passive environmental strategies including high-performance glazing, orientation-specific shading systems, compact massing, and wind- and buoyancy-driven natural ventilation. Building performance was evaluated under present-day conditions and projected 2080 weather data. Adaptation scenarios included an open courtyard, fixed glazed roof, operable glazed roof, operable glazed roof with external shading louvers, and alternative louver configurations. Energy Use Intensity (EUI), operational carbon emissions, and thermal discomfort hours were used as performance metrics. Results show that future climates reduce heating demand while increasing cooling loads, shifting energy consumption patterns. Under the projected 2080 climate, the baseline open-courtyard configuration achieved an EUI of 66 kWh/m²·yr and 1,110 thermal discomfort hours. The highest-performing adaptation strategy consisted of an operable glazed roof integrated with shading louvers, reducing EUI to 61 kWh/m²·yr, operational carbon emissions from 19,530 to 18,129 kgCO₂e, and thermal discomfort hours to 820. The enclosure system also improved courtyard environmental control while preserving natural ventilation. The findings demonstrate that adaptive courtyard enclosures can enhance the energy and comfort performance of naturally ventilated office buildings under future climates. The study highlights the value of integrating future weather files into performance analysis and provides a framework for evaluating retrofit and design strategies for courtyard typologies.