Although Web-based personal health records (PHRs) have been widely deployed, the existing ones have limited intelligence. Previously, we introduced expert system technology and Web search technology into the PHR domain and proposed the concept of an intelligent PHR (iPHR). iPHR provides personalized healthcare information to facilitate users' daily activities of living. The current iPHR is passive and follows the pull model of information distribution. This paper introduces triggers and monitoring into iPHR to make iPHR become active. Our idea is to let medical professionals pre-compile triggers and store them in iPHR's knowledge base. Each trigger corresponds to an abnormal event that may have potential medical impact. iPHR keeps collecting, processing, and analyzing the user's medical data from various sources such as wearable sensors. Whenever an abnormal event is detected from the user's medical data, the corresponding trigger fires and the related personalized healthcare information is pushed to the user using natural language generation technology, expert system technology, and Web search technology.