The COVID-19 pandemic illuminated the need for urban community colleges to utilize an adaptive leadership approach to thrive during times of uncertainty. Adaptive leaders encourage team members to address problems through new ways of thinking to meet organizational goals. The community college sector, especially institutions in urban environments, has utilized adaptive leadership throughout its history to best meet the needs of its students. It is against this background that urban community colleges adapted to the COVID-19 pandemic by reconceptualizing career programs to be completed in virtual spaces, hosting COVID-19 testing and vaccination centers on campus, and ensuring that students had access to faculty and staff in a digital learning environment. In this chapter, we highlight the importance of adaptive leadership in urban community colleges and provide examples from urban community college leaders on how they utilize adaptive leadership to meet new challenges.