OBJECTIVE The majority of the literature on stress and blood pressure (BP) concerns the increased risk of cardiovascular morbidity and mortality from high BP. Because the sympathetic nervous system is critical to the maintenance of orthostatic BP, it was hypothesized that older adults who have experienced more stressful life events (SLEs) would be more likely to show impaired recovery of BP in response to orthostatic stress. METHODS A total of 3,765 participants (Mage = 61.6 years, SD = 8.2; 54% female) from the first wave of The Irish Longitudinal Study on Ageing (TILDA) were included in the current analysis. Exposure to lifetime SLEs was ascertained by self-completion questionnaire, and beat-to-beat orthostatic BP measurement was carried out. Individuals who failed to recover at least 95% of their baseline BP by 60 s post stand were characterized as having impaired orthostatic BP recovery. RESULTS An independent, dose-response relationship between the number of SLEs reported and the odds of impaired systolic BP recovery was observed after adjustment for covariates (1 event: odds ratio [OR] = 1.19, 95% confidence interval [CI] [0.98, 1.45], p = .078; 2 events: OR = 1.33, 95% CI [1.03, 1.73], p = .031; 3 or more events: OR = 1.56, 95% CI [1.12, 1.73], p = .009). This relationship was not evident for diastolic BP recovery. CONCLUSIONS The reporting of a higher number of SLEs is associated with greater risk of impaired systolic BP recovery from orthostatic stress. Potential clinical implications include an increased risk of cerebral hypoperfusion, which predisposes older adults to falls, faints, and changes in cognitive status.