Over the past half century, the relationship between working and learning has changed in profound ways that have made it more difficult for students, especially students from low-income backgrounds, to attain the right mix of work experience and schooling necessary to qualify for entry-level jobs with a future. The report highlights that college and university leaders must weigh the unique challenges low-income working students face and marshal more resources to improve these students’ academic and career outcomes. Additional attention must be focused on building stronger connections between education and work beginning in the K–12 years, improving career counseling and guidance in postsecondary institutions, and improving support services for working learners, with a special emphasis on meeting the needs of low-income students.