There is a well-recognized need for a shift to proactive asthma care given the impact asthma has on overall healthcare costs. The demand for continuous monitoring of patient’s adherence to the medication care plan, assessment of environmental triggers, and management of asthma can be challenging in traditional clinical settings and taxing on clinical professionals. Recent years have seen a robust growth of general purpose conversational systems. However, they lack the capabilities to support applications such an individual’s health, which requires the ability to contextualize, learn interactively, and provide the proper hyper-personalization needed to hold meaningful conversations. In this paper, we present kBot, a knowledge-enabled personalized chatbot system designed for health applications and adapted to help pediatric asthmatic patients (age 8 to 15) to better control their asthma. Its core functionalities include continuous monitoring of the patient’s medication adherence and tracking of relevant health signals and environment data. kBot takes the form of an Android application with a frontend chat interface capable of conversing in both text and voice, and a backend cloud-based server application that handles data collection, processing, and dialogue management. It achieves contextualization by piecing together domain knowledge from online sources and inputs from our clinical partners. The personalization aspect is derived from patient answering questionnaires and day-to-day conversations. kBOT’s preliminary evaluation focused on chatbot quality, technology acceptance, and system usability involved eight asthma clinicians and eight researchers. For both groups, kBot achieved an overall technology acceptance value of greater than 8 on the 11-point Likert scale and a mean System Usability Score (SUS) greater than 80.