Community-based instruction (CBI) is one type of community experience in which students with disabilities work toward instructional goals while engaged in activities occurring in a natural environment outside of a typical school setting (Hoover, 2016; Rowe et al., 2015). Educators who implement CBI capitalize on their students' time in the community to ensure that students are doing more than simply experiencing a new setting; during CBI, students learn and generalize skills and knowledge that will support their engagement in that setting and future success. The steps outlined in this article describe how educators can apply research-based approaches to progress monitoring that take into consideration the instructional methods, behaviors, situational factors, and informal assessment methods that are unique to CBI. As a systematic approach to collect data on student performance and learning while in the community, progress monitoring during CBI can provide important insights into students' learning as students prepare to be contributing citizens in their communities.