PURPOSE This article investigates how continuing care retirement community (CCRC) residents define transitions between levels of care. Although older adults move to CCRCs to “age in place,” moving between levels of care is often stressful. More than half a million older adults live in CCRCs, with numbers continually increasing; yet, no studies address transitions between levels of care in these communities. DESIGN AND METHODS I completed 23 months of live-in observation and conducted 35 face-to-face in-depth interviews with CCRC residents across 3 levels of care. I performed a thematic analysis of observation notes and interview transcripts. RESULTS Residents perceived transitions as both disempowering and final. They discussed decreases in social networks that occurred after such moves. Resident-maintained social boundaries exacerbated these challenges. IMPLICATIONS Although the transition to institutional living is one of the most important events in older persons’ lives, transitions within CCRCs also are consequential especially because they are coupled with declining functional ability. These findings may inform policy for retirement facilities on topics such as increasing privacy, challenging social boundaries, and educating residents to prepare them for transitions.