ABSTRACT Purpose Habitual strength and power-demanding activities of daily life may support the maintenance of adequate lower extremity functioning with aging, but this has been sparingly explored. Hence, we examined whether the characteristics of free-living sit-to-stand (STS) transitions predict a decline in lower extremity functioning over a 4-yr follow-up. Methods A total of 340 community-dwelling older adults (60% women; age 75, 80, or 85 yr) participated in this prospective cohort study. At baseline, a thigh-worn accelerometer was used continuously (3–7 d) to monitor the number and intensity of free-living STS transitions. A decline in lower extremity functioning was defined as a drop of ≥2 points in the Short Physical Performance Battery (SPPB) from baseline to follow-up. Maximal isometric knee extension strength was measured in the laboratory. Results Eighty-five participants (75% women) declined in SPPB over 4 yr. After adjusting for age, sex, and baseline SPPB points, higher free-living peak STS angular velocity (odds ratio (OR), 0.70; 95% confidence interval (CI), 0.52–0.92, per 20°·s−1 increase) protected against a future decline. When adjusting the model for maximal isometric knee extension strength, the statistical significance was attenuated (OR = 0.72; 95% CI = 0.54–0.96, per 20°·s−1 increase). Conclusions Performing STS transitions at higher velocities in the free-living environment can prevent a future decline in lower extremity function. This indicates that changes in daily STS behavior may be useful in the early identification of functional loss. Free-living peak STS angular velocity may be a factor underlying the longitudinal association of lower extremity strength and performance.