The federal Pell Grant was designed to help low-income students pay for college. But over the past two decades, a growing share of middle-income students have become eligible for the program. This was not policymakers' explicit goal. This report examines how the program came to increasingly provide students from middle-income families with grants, particularly those earning between $50,000 and $60,000, focusing on changes that occurred between the 1995-96 and 2018-19 academic years. It concludes with recommendations for policymakers to improve the targeting of the Pell Grant program.