There is little in the literature on dental restoration breakage in the aviation environment since reports of problems in combat aviators in War World II. We report two cases of dental fractures during acute exposure to a hypobaric environment. Case 1 was a young officer who suffered an amalgam restoration breakage during a 25,000-ft decompression chamber simulation. Case 2 occurred in an experienced aviator who had a tooth cusp fracture in a molar with a defective amalgam restoration during an unpressurized helicopter flight to 18,000 ft. In both cases, after removing the defective fillings, deep secondary caries were found; both teeth were successfully restored. Because hard-tissue tooth fracture during a high-altitude flight is a rare event, few flight surgeons or dentists are familiar with this phenomenon. We recommend regular dental examinations with careful assessment of previous dental restorations in aircrew subject to decompression.