Accurate Blood Pressure (BP) measurement is vital for appropriate diagnosis and management of cardiovascular risk. However, questions remain on the accuracy of cuff BP compared with invasive (intra-arterial) BP. Moreover, the critical physiological factors that are associated with inaccuracy of cuff BP and estimated central BP are still not fully understood. Our group has recently conducted a series of individual participant data meta-analyses, and targeted physiology studies to address these questions and build knowledge on possible ways to improve the accuracy of BP measurements. The aim of this review is to detail this work and briefly discuss future directions for the field.