Studies examining the association between laboratory measures of stress-related cardiovascular (CV) reactivity and responses to psychological challenges in the natural environment have yielded mixed results. Frequently, single laboratory tasks have been used to predict responses to natural stressors on a single occasion of measurement. Because aggregation broadens the range of stimuli sampled and reduces measurement error, laboratory-to-life generalizability should be more easily detected when multiple predictor and criterion observations are used. Sixty students in a public speaking course were administered multitask assessments of CV reactivity during two laboratory sessions and during two in-class public speech assignments. CV responses to the classroom speeches were greater among those who showed larger responses in the laboratory, and these associations became stronger as measures were aggregated across multiple samples of behavior. These results support the generalizability of CV reactivity as a measure of individual difference, and they help to shed light on previous inconsistent findings in this area.