Special education professionals are charged to develop relevant, compliant, and legally defensible IEPs for transition-age students with disabilities. This charge is intensified as educators strive to provide plans that will genuinely prepare students for postsecondary education, employment, and independent living. This manuscript demonstrates how annual goals align with postsecondary goals through triangulation of (a) linking transition and academic assessments, (b) embedding industry and content standards related to postsecondary goals, and (c) conducting skill and knowledge gap analyses. This process ensures educators that annual goals are genuine and relevant to postsecondary goals, legally defensible, and meet the standards of compliance. (Contains 4 tables and 3 figures.)