Objective: In Spring 2020 when COVID-19 hit, community colleges moved almost all classes online. This disruption impacts recent math reforms, including contextualization, raising concerns about sustained faculty and institutional leadership commitment. This study investigated how community college faculty teaching contextualized math courses adapted their instruction in response to COVID-19-related disruptions and how community college and instructional leadership addressed math contextualization efforts in response to COVID-19. Methods: Using multiple case studies, we conducted interviews with faculty and institutional leaders from two large community colleges in a Midwestern state. We also integrated field notes, observations, lesson plans, project documentation, and other contextual information as complementary data. Results: Three themes revealed how faculty and institutional leaders navigated the process of adapting contextualization efforts throughout the pandemic: reaching out to create community remotely, reimagining contextualization or pushing the pause button, and skilling up to persist through and toward change. Contribution: This study provides insight into the unique challenges and innovations due to sudden yet enduring disruptions that impact instruction, faculty development, and institutional support around instructional reform in the community college. This research informs faculty and institutional leaders navigating sustained efforts around math reform to identify actions to help institutions and their faculty continue advancing high-impact approaches and initiatives to math instruction in any environment.