Objective: Connected blood pressure (BP) monitors provide reliable data when used properly. Our objective was to analyse the engagement of real-world users with self-measurements. Methods: We included adult first-time users of a connected BP monitor from July 2019 to March 2021. They were categorized as persistent users if they continued to use the device between 311 and 400 days after inclusion. We defined a criterion to analyse the timing of self-measurements: at least 12 measurements performed within three consecutive days, at least once every 90 days. Persistent users were clustered by state sequence analysis according to the consistency of their BP monitor measurement timing with this criterion during 1 year of follow-up. Results: Among the 22 177 included users, 11 869 (54%) were persistent during the first year. Their use was consistent with the timing criterion 25% (median) of this time (first and third quartiles: 0%, 50%) and four patterns of use were identified by clustering: 5215 persistent users (44%) only performed occasional sparse measurements, 4054 (34%) complied at the start of follow-up up to eight cumulated months, 1113 (9%) complied at least once during later follow-up up to eight cumulated months, and the remaining 1487 (13%) complied nine or more cumulated months of follow-up. Conclusion: Although connected BP monitors can collect a high volume of data, the real-life timing of self-measurements is far from recommended schedules. We must promote the use of BP monitors as recommended by guidelines and/or learn to analyse more occasional and sparse measurements.