Introduction: Accommodations are essential for the successful participation of individuals with visual impairments in post-secondary education and employment. Passive experiences with accommodations in school, plus a complex advocacy process warrant the need to support students to engage in the accommodations process. Methods: Four high school students with visual impairments were taught the Student Self-Accommodation Strategy. A parallel multiple-case design was used to determine how and how well the participants learned and used the strategy and to investigate their development of metacognitive knowledge and self-regulated learning (SRL) skills. Results: The participants all learned the strategy to varying extents. The cross-case analysis revealed that recall and understanding the purpose of the strategy supported strategy performance but were not associated with in-class use of the strategy. Additionally, participants did not experience changes with metacognition or SRL; however, they did demonstrate metacognitive knowledge on multiple data sources, with few demonstrations of SRL. Discussion: Findings indicate that the Student Self-Accommodation Strategy is accessible to students with visual impairments. Three factors seemed to be associated with the learning and use of the strategy: verbal and reasoning skills, achievement, and emotional-behavioral regulation. Metacognition and SRL can positively affect students with visual impairments. Implications: Future work with the Student Self-Accommodation Strategy should incorporate in-class strategy coaching and an explicit investigation of the factors that seemed to influence strategy learning and performance. Research and practice should give greater attention to metacognition and SRL for students with visual impairments.