A wireless communication system and related techniques and apparatuses are disclosed that predict future disconnections or other connection impairments with end-user portable devices in advance so that service interruptions can be handled more gracefully. The system can predict the loss of service based on user-usage information associated with the portable device, such as the current GPS location of the device, its direction and velocity of travel, a user calendar, user habits and other information, such as the time of day, weather conditions, or wireless network coverage maps. An impairment handling method is selected that alters the content presented by the portable device. The impairment handling method is executed by the system upon detecting the impairment of the wireless connection so that the content is altered during occurrence of the impairment. The alteration of the content is done to mitigate the user-perceived effect of the impairment.