When chloroplasts are damaged by reactive oxygen species, they can be degraded to protect cells or to redistribute nutrients, but these pathways remain poorly understood. In this issue, Fisher et al. (pp. 248-264) have demonstrated that the reactive oxygen species singlet oxygen can trigger chloroplast swelling, changes in the internal structures of chloroplasts, and chloroplast interactions with the central vacuole prior to degradation. Such structural changes may be a mechanism by which a cell can target damaged or senescing chloroplasts for turnover.