Maloney High School, in Meriden, CT, has made significant strides in increasing underrepresented students' access to challenging courses, with content ranging from college preparation to career-oriented learning. Creative student-and-family-centered strategies, which incorporate quantitative data and individual counseling, have increased awareness of these courses and spurred dramatic enrollment increases among all learners, especially among Black and Latinx/Hispanic students and English Language Learners. Meriden district and school leaders know that equitable access to advanced courses does not always result in equitable outcomes from them. The team is now focused on ensuring that underrepresented students enrolling in these courses have the support to complete and excel in them. This case describes the school's current outreach and support strategies and concludes with important questions for school leaders and design teams seeking to address similar challenges. [For the corresponding Case Studies in High School Redesign, see ED626303 and ED626305.]