Self-assessment has been shown to have positive effects on students’ self-regulated learning strategies and academic achievement. However, self-assessment and self-assessment instruction are under-researched areas among students with intellectual disability. This data-driven qualitative study aimed at examining the self-assessment expressions students with intellectual disability documented in their learning diaries and how the teacher and teaching assistants used video recordings to facilitate students’ self-assessments in one Finnish special needs education class. The naturally occurring research data consisted of both students’ tablet-based learning diaries (N = 6) and video recordings of students’ self-assessment situations (N = 17). The results show that students’ self-assessment expressions varied from short and vague expressions to argumentative and reflective assessments. The use of video recordings served various functions, such as directing and instructing students, demonstrating assessment and providing feedback. The outcomes of this study demonstrate how the self-assessment practices of students with intellectual disabilities can be facilitated by using video.