This study examined whether there are differences between Israeli students with learning disabilities (LD) and their typically developing peers with regard to their 21st-century skills according to their self-report and whether the differences between the two groups are greater in postsecondary education than in high school--an aim that had not been examined in depth in previous research. Findings suggest that overall (beyond type of learner), in most skills, postsecondary education students reported higher scores than high school students on questionnaires designed for self-assessment of 21st-century skills. Second, students with LD exhibited lower scores in most 21st-century skills than their peers. Third, a comparison of the gaps in 21st-century skills between students with LD and their peers in each of the examined educational settings (i.e., high school vs postsecondary education) revealed that some of the gaps expand over the years, resulting in differences in additional skills. Results are discussed in the context of educational environment and its role in cultivating 21st-century skills and preparing students for integration into the labor market.