Abstract With the rise of awareness of health and well-being in cities, urban environmental analysis should expand from energy performance to new environmental quality-based considerations. The limited potential to annually evaluate outdoor thermal comfort, predominant among these considerations, has restricted the exploration of the interrelations between urban morphology and annual energy performance. This study aims to bridge this gap by capitalizing on the new capabilities of Eddy3D – a Grasshopper plugin which enables effective calculations of hourly microclimatic wind factors via OpenFOAM which in turn are used to generate annual outdoor thermal comfort plots. Using this method, a parametric study was conducted for different typology and density scenarios in three different hot climatic contexts in Israel. The automated analytical workflow evaluated a total of 60 design iterations for their energy balance, outdoor thermal comfort autonomy (OTCA) and self-shading levels using the shade index. The high correlation found here between the annual shade index and the OTCA, across all climatic contexts, shows the potential of the shade index to serve as an effective indicator, in these contexts, for comparative or optimization outdoor comfort studies. Further results are both the superiority of the courtyard typology in both energy and outdoor comfort studies, and the contrasting impact of higher density on the annual energy balance (lower performance) and outdoor thermal comfort (higher performance) in hot climates. The annual plots of both the energy balance and OTCA reveal various seasonal and monthly trends in the three different climatic zones which can lead to localized and seasonal urban design strategies.