This paper is a critical examination of four factors that affect widespread adoption of computer-based interventions in general and adaptive instructional systems (AISs) in particular within the Philippine context: Despite government and private sector efforts, hardware diffusion in schools has not reached critical mass. The poorest sectors of society have very limited Internet access. The curriculum tends to focus on computer literacy skills and is generally unable to use information and communication technologies to support specific subjects. Finally, teachers lack the preparation and, as a consequence, the confidence to use technology in innovative ways. The study-from-home necessitated by the COVID-19 pandemic would have been an ideal opportunity to maximize the impact of computer-based interventions such as AISs as these technologies have been shown to compensate for weak teacher-led instruction. However, AISs demand the very same resources that the Philippines educational system does not have, making such deployments impossible. This paper ends with a challenge to design AISs to operate under these difficult circumstances in order to maximize the benefits that they bring to education.