High school is becoming the next frontier for after-school advocates. The conceptual and practical leaps from programming for elementary and middle school students to high school students are significant, and the marketing challenges are huge. Arguing persuasively for investments in this population requires revisiting almost every strategic decision made, from public education to policy framing to partnership development. To support policy makers, program leaders and advocates in making decisions related to high school after-school, this commentary summarizes what we know and answers some basic but important questions. Conversations with Kathy Lewis, deputy superintendent for Child, Youth and Family Services in the California Department of Education, and Milbrey McLaughlin, of Stanford University, help us illustrate and bridge the policy and research perspectives on high school programming.