The majority of Chicago Public Schools students are not attaining the ACT scores they are aiming for, which they need to qualify for scholarships and college acceptance. In this report, CCSR researchers look at the reasons behind students' low performance and what matters for doing well on this test. CPS students are highly motivated to do well on the ACT, and they are spending extraordinary amounts of time preparing for it. However, the predominant ways in which students are preparing for the ACT are unlikely to help them do well on the test or to be ready for college-level work. Students are training for the ACT in a last-minute sprint focused on test practice, when the ACT requires years of hard work developing college-level skills. This study relies on qualitative and quantitative data for a cohort of students who were CPS juniors in 2005. This includes test scores from eighth to eleventh grade, student transcripts, CCSR surveys, and multiple interviews of students and teachers at three Chicago high schools. The report also incorporated 2007 data on CPS juniors and teacher surveys.