Hypertension even when controlled, may accelerate arterial stiffening and impair the ability of the cerebrovasculature to increase blood flow to support neural activity, i.e., neurovascular coupling (NVC). Optimal NVC depends on continuous, nonpulsatile flow, which is partially determined by extra- and intracranial vessel function. We sought to compare extra- and intracranial hemodynamics during cognitive activity (Stroop task) in 30 middle-aged, well-controlled medicated hypertensive and 30 age-, sex-, and body mass index (BMI)-matched nonhypertensive adults (56 6 years, 28.2 2.9 kg/m 2 BMI; 32 men). Aortic and carotid (single point) pulse wave velocity (PWV) were assessed via tonometry and ultrasound, respectively. Carotid and middle cerebral artery (MCA) blood velocity pulsatility were measured via ultrasound and Doppler. Prefrontal cortex (PFC) oxygenation was measured via tissue saturation index (TSI) using near-infrared spectroscopy. Accuracy and reaction times were computed to assess cognitive performance. Stroop performance was similar between groups (P 0.01). Aortic and carotid PWV increased, carotid flow pulsatility decreased (P 0.01), and MCA flow pulsatility and PFC TSI were maintained during Stroop (P 0.01). Our findings indicate that middle-age adults with medically controlled hypertension and adults without hypertension demonstrate similar intra- and extracranial cerebrovascular reactivity during cognitive engagement. Despite increases in large artery stiffness, middle-aged adults with controlled hypertension and without hypertension exhibit reductions in extracranial flow pulsatility during cognitive engagement that may be part of a concerted cerebrovascular response to support downstream cerebral oxygenation and overall NVC. NEW & NOTEWORTHY Hypertension is associated with accelerated arterial stiffening, which may alter extra- and intracranial vascular reactivity during cognitive activity and impair neurovascular coupling. Middle-aged adults with medicated hypertension exhibit similar neurovascular coupling and extra-/intracranial vascular reactivity during sustained cognitive activity. Extracranial modulation of central hemodynamics may be an important component of optimal neurovascular coupling.