One crucial decision that middle schoolers (and their families) make is where they will attend high school. Many districts employ school choice systems designed to allow students to pick a high school that will meet their needs and interests. Yet most students prefer high schools that are close to home, and for youth in low-income neighborhoods, this often means attending a more disadvantaged, lower performing school (Nathanson et al. 2013). Youth who defy these odds and choose a competitive high school instead have much to gain. Cullen et al. (2005), for instance, found that Chicago public middle school students who chose to attend a higher-achieving high school were substantially more likely to graduate. However, even as eighth graders, these students already differed in many ways from their peers who chose a neighborhood school--they had better self-reported grades and higher expectations for the future, felt more prepared for high school, and were more likely to have spoken with their parents about what school to attend. These findings raise the question of how we can prepare more disadvantaged students to take the many steps necessary-throughout the middle school years-to successfully transition to a competitive, high-quality high school that can ultimately launch them toward college and careers. The Washington, DC-based Higher Achievement program is taking on this challenge. Higher Achievement targets rising fifth and sixth graders from "at-risk communities" and serves them throughout the middle school years. Its goal is to strengthen participants' academic skills, attitudes and behaviors, reinforce high aspirations and help students and their families navigate the process of applying to and selecting a high-quality high school. In 2006, the authors began a comprehensive multi-year evaluation of Higher Achievement to test its impact on participants' academic performance, attitudes and behaviors and on their high school enrollment. The evaluation used random assignment-the most rigorous design available to researchers-to assess program impacts. This brief summarizes the study's findings. Findings suggest that the program does appear to expand the options available to its students by making them more likely to apply to and attend private schools and less likely to apply to and attend weaker public magnet and charter schools. This, in turn, may position youth for better outcomes in high school and beyond. [This research was made possible by grants from The Atlantic Philanthropies, Bank of America, the Smith Richardson Foundation, the Spencer Foundation, The Wallace Foundation and the William T. Grant Foundation.]