Students with learning disabilities seek postsecondary education at rates comparable to their peers yet lag behind on retention and graduation rates. This research used InQuiry methodology to analyze 44 individual perspectives from multiple K12 and postsecondary stakeholders. Quantitative data analysis generated a four-factor solution, identifying four "family groups" of participants. Subsequent interviews yielded qualitative data to inform the context for each group perspective. Families agreed on broad themes of self-advocacy and the need for intentional communication and collaboration between secondary and postsecondary settings, yet emphasized varying responsibilities and opportunities related to addressing these priorities in both K12 and college environments. The study generated promising practices and identified barriers to transition success from practitioners for practitioners.