Research has indicated that the “observing” facet of mindfulness fits a hierarchical factor structure in which specific facets relate to a general mindfulness factor, and correlates with well-being, only among meditators. We extended this research by testing whether observing functions differently among meditators in terms of buffering the effects of stress on distress. Participants (N = 190 including 78 meditators) completed measures of life events, mindfulness, and distress symptoms. As hypothesized, there was a significant interaction of observing × stress × meditation, such that the effect of stress on distress was smallest among meditators scoring high on observing. Additional research is needed to test alternate interpretations (e.g., self-selection of meditation as an enjoyable practice by those who can observe in an adaptive manner), but the results suggest that meditation helps people learn to observe internal and external experience in an unbiased manner lending itself to constructive coping.