Executive functions (EF) are a collection of cognitive domains governing task initiation, motor planning, attention, and goal-oriented action. Difficulties with EF have marked impacts on adaptive living skills, learning outcomes, and quality of life for people with cognitive and psychosocial disabilities, as well as the broader population. While there is considerable research interest in EF training intervention for disabled school-aged children and other disabled populations, very few studies explore metacognitive intervention for people with cognitive disabilities. Metacognition comprises conscious beliefs and strategies around task management and goal setting. Metacognitive awareness has been shown to mediate effects of executive function on self-regulated learning, and metacognitive interventions have shown promise in general education, military training, and medical practice. Using principles of ability-based design, role-fluidity, and agent-based modeling, this dissertation work explores the features and conditions essential to metacognitive intervention for autistic people and people with ADHD. The researcher uses a Critical Disability Studies lens to evaluate testimonials of executive function experiences from autistic adults and children. These insights inform the design of a system that allows the researcher to investigate the efficacy and transferability of explicit metacognitive strategy instruction for undergraduate students of all neurotypes. The researcher developed a VR toolkit for real-time measurement of executive function and metacognitive strategy development that can be adapted for any context. This system's output was found to be statistically comparable to traditional measures of executive function. The researcher found supporting evidence that explicit instructional material explaining executive function and metacognition in relation to problem-solving experiences influenced participant self-concept and awareness of personal traits and cognitive processes. This dissertation work is grounded in critical understandings of the onto-epistemology of disabled embodiment and agency. The researcher demonstrates a critique of technological interventionism through the development of a technological intervention designed with applied theories of Crip Technoscience, Diffraction, Phenomenology, and Digital Embodiment. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]