Students of all ability levels, including those identified with intellectual disabilities (ID) and autism spectrum disorder (ASD), can benefit from improving their ability to take their knowledge out of the lower-order learning realm and transferring or applying into higher-order learning. Practical application of knowledge is important for post-secondary success of students with ID and ASD, especially in a functional manner that will improve their daily lives. As an educator working in special education for nine years, I have observed a lack of practical application of knowledge opportunities for these students to perform the conceptual definitions of functional sight-words. I have also observed an absence of consistent assessment procedures to measure student’s practical application of functional life skills in a realistic environment. To address these, I designed a research study using the situated learning theory and revised Bloom’s Taxonomy that enhanced the Edmark Functional Word Series curriculum (EFWS) to improve its practicality and generalization of functional sight-words. Using a concurrent mixed methods research design, quantitative and qualitative data were collected and analyzed concurrently. A sample of 25 participants enrolled in a special education self-contained program completed a 16 week curricular enhancement of the EFWS that included a self-made functional life skills measurement tool. Findings indicated that the increase of situated learning strategies and opportunities within instruction was effective in improving student learning, including improvement of practical application performance. Findings also indicated that increases seen throughout the study are a direct result of targeted instructional practices designed to expand knowledge acquisition out of the lower-order learning realm and into higher-order learning. The study concludes with recommendations for practice and future research.