This paper presents an intelligent system designed to increase the treatment adherence of hypertensive patients. The architecture was developed to allow communication among patients, physicians, and families to determine each patient’s medication intake and self-monitoring of blood pressure rates. Concerning the medication schedule, the system is designed to follow a predefined prescription, adapting itself to undesired events, such as mistakenly taking medication or forgetting to take medication on time. When covering the blood pressure measurement, it incorporates best medical practices, registering the actual values in recommended frequency and form, trying to avoid the known “white-coat effect.” We assume that taking medicine precisely and measuring blood pressure correctly may lead to good adherence to the treatment. The system uses commercial consumer electronic devices and can be replicated in any home equipped with a standard personal computer and Internet access. The resulting architecture has four layers. The first is responsible for adding electronic devices that typically exist in today’s homes to the system. The second is a preprocessing layer that filters the data generated from the patient’s behavior. The third is a reasoning layer that decides how to act based on the patient’s activities observed. Finally, the fourth layer creates messages that should drive the reactions of all involved actors. The reasoning layer takes into consideration the patient’s schedule and medication-taking activity data and uses implicit algorithms based on the J48, RepTree, and RandomTree decision tree models to infer the adherence. The algorithms were first adjusted using one academic machine learning and data mining tool. The system communicates with users through smartphones (anytime and anywhere) and smart TVs (in the patient’s home) by using the 3G/4G and WiFi infrastructure. It interacts automatically through social networks with doctors and relatives when changes or mistakes in medication intake and blood pressure mean values are detected. By associating the blood pressure data with the history of medication intake, our system can indicate the treatment adherence and help patients to achieve better treatment results. Comparisons with similar research were made, highlighting our findings.