In the field of urban design, many designers laud generative tools for their insightful power, especially given the complex urban issues that we face today. For many, these tools are especially helpful in wading through, distilling, and prioritizing the large economic, social, and environmental datasets that are available for urban sites and for revealing proposals not typically considered in nongenerative urban design processes. Some think that generative tools have the power to shift the fundamental role of the urban designer but at the same time, there are concerns about the potential loss of designer agency. This study is based on the premise that it is necessary to critically evaluate emerging tools like those employed in generative design before they are widely adopted into mainstream practice. Thus, with this work, we studied the role of one generative tool – Spacemaker1 – to better understand the potential challenges and benefits of integrating these techniques into design workflows. We found that, in its current form, this tool cannot replace the detailed work of designers but can, instead, assist them to think outside of the box and with mundane, repetitive tasks. Furthermore, we found promise in a more hybridized future with a co-created design process.