The behavior of 2 spectacled bears (Tremarctos ornatus) was studied at Wroclaw Zoo (Poland), where they were housed in a very small outdoor enclosure, and then in a separate study after transfer to a large naturalistic exhibit at Chester Zoo (CZ; United Kingdom). The studies combine to form an opportunistic “experiment” on the effects of transfer on zoo animals. This situation provided a unique opportunity for a closer investigation of known behavior problems and their causation. In part 1 of the study, at Wroclaw Zoo, the median amount of time devoted to stereotypical movements was 57 min/h. After the move to CZ, immediate changes in behavior were reported in 1 individual, for whom the stereotypy was eradicated. The other bear continued performing repetitive behavior of high intensity and only used a small area of the large enclosure. Signs of dental problems were subsequently observed in both bears, and so a dental examination was carried out, resulting in multiple extractions. After treatment, the amount of time that the bear with ongoing behavior problems spent stereotyping reduced significantly, and foraging increased. Our data suggest the bears' stereotypic behavior occurred not only in response to an understimulating environment in their old enclosure but also perhaps in association with medical conditions in one of the bears. Although other factors could have contributed to the observed reduction in stereotypy, it is clear that further investigation is needed into the effects of pain and physical condition on stereotypy in animals.