The U.S. Department of Education (Department) issued a Dear Colleague Letter (Letter) on November 16, 2015, to "clarify that an individualized education program (IEP) for an eligible child with a disability under the Individuals with Disabilities Education Act (IDEA) must be aligned with the State's academic content standards for the grade in which the child is enrolled" (Yudin & Musgrove, 2015, p. 1). The Department's mission is to raise expectations for students with disabilities, many of whom are currently receiving a less challenging curriculum than general education students. Aligning IEP goals with grade-level content standards is an important way to support this mission, especially for students who are placed outside of general education settings. This article analyzes the contradictory sources of sample IEP goals to which the Department referred practitioners and discusses the legal risks associated with aligning an IEP goal to a single standard rather than to a range of standards. Recommendations are provided to school leaders regarding policies and IEP forms to ensure that they facilitate alignment to grade-level standards in a way that also supports IDEA-mandated individualization of IEP goals.