With mobile devices being today one of the main sources of Internet traffic, and the increasing amount of mobile services and applications, the importance of monitoring quality of service for this platform cannot be ignored. Such is the motivation behind the Adkintun Mobile project, attempting to characterize mobile QoS through passive monitoring of devices. The first phase of our project showed great results for our passive approach, however, we concluded that some active testing may be necessary for a more accurate characterization of service quality, but the device context is needed to best establish when to test. In this work we describe our efforts towards context-based active testing, including the development of our monitoring middleware, that through recording of status changes for different aspects of the system in the device, will allow us (and other developers) to clearly identify the context when QoS issues occur.