Cognitive rehabilitation has the capacity to empower persons with brain-injuries and help them achieve heightened functional, personal, and social interactions within their environments. Interventions aimed at compensation for deficits and adaptation to cognitive disability can be aided through the use of assistive technology devices (ATD's). ATDs allow for their users to experience greater levels of independence, as well as social and vocational participation, which leads to a higher quality of life. The ISAAC system is a small, individualized, wearable cognitive prosthetic assistive technology system. Being fully individualized and very easy to use makes this system adaptable to, and appropriate for, patients with a wide variety of cognitive disabilities ranging from individuals with developmental disabilities to high functioning survivors of brain injury. The current article will discuss two cases that illustrate the effectiveness of the ISAAC system in assisting patients with generalization of rehabilitation to their home environments. Both patients incurred significant cognitive impairment, for which they were able to successfully compensate with the assistance of their ISAAC systems. These two case studies are typical examples of the functional independence that can be achieved through the use of the ISAAC system. When patients are properly selected for use of this system, appropriate content is authored, and sufficient training on the system is provided, the ISAAC system can prove very effective at improving patients' functional independence.