Despite extensive transition provisions in the U.S. Individuals with Disabilities Education Act (IDEA), the post-school outcomes for students with disabilities continue to be disappointing. The IDEA designated those transition provisions as priority targets for federal and state compliance monitoring to assure that schools are attaining the goal of successful post-school transition for students with disabilities. Yet, we question if the compliance monitoring approach, indicator targets, and data collection requirements are appropriate and adequate to gauge post-school success. We provide a critical examination of the transition performance monitoring indicators and propose recommendations for policy and praxis, including culturally responsive data disaggregation by ethnicity and race. These policy proposals, coupled with effective preservice and inservice professional development praxis, will enhance successful transition outcomes for students with disabilities.