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With increasing urbanization, climate change poses an unprecedented threat, and climate-sensitive urban management is highly demanded. Mitigating climate change undoubtedly requires smarter urban design tools and techniques than ever before. With the continuous evolution of geospatial technologies and an added benefit of analyzing and virtually visualizing our world in three dimensions, the focus is now shifting from a traditional 2D to a more complicated 3D spatial design and assessment with increasing potential of supporting climate-responsive urban decisions. This paper focuses on using 3D city models to calculate the mean radiant temperature (Tmrt) as an outdoor thermal comfort indicator in terms of assessing the spatiotemporal distribution of heat stress on the district scale. The analysis is done to evaluate planning scenarios for a district transformation in Montreal/Canada. The research identifies a systematic workflow to assess and upgrade the outdoor thermal comfort using the contribution of ArcGIS CityEngine for 3D city modeling and the open-source model of solar longwave environmental irradiance geometry (SOLWEIG) as the climate assessment model. A statistically downscaled weather profile for the warmest year predicted before 2050 (2047) is used for climate data. The outcome shows the workflow capacity for the structured recognition of area under heat stress alongside supporting the efficient intervention, the tree placement as a passive strategy of heat mitigation. The adaptability of workflow with the various urban scale makes it an effective response to the technical challenges of urban designers for decision-making and action planning. However, the discovered technical issues in data conversion and wall surface albedo processing call for the climate assessment model improvement as future demand. [ABSTRACT FROM AUTHOR]