Assignment to remediation in college poses a significant barrier to degree attainment. Computer-mediated delivery of remedial mathematics shows promise as a means of enabling students to accelerate through math remediation and become college-ready. In Tennessee, this type of reform was for some time offered as a course to both high school and college students. Yet the high school students were much more likely to complete the course in one semester. This study makes use of site visit data collected at three community colleges and four high schools in Tennessee in 2015 to explore how the institutional context of the high schools compared with that of the colleges in ways that may have affected the implementation and efficacy of computer-mediated mathematics. Broadly, the high schools maintained structures and enacted classroom practices to foster student success under the premise that such students are unlikely to have autonomous, self-directed study habits. Community colleges, on the other hand, generally sustained policy and practice based on the notion that a community college student is autonomous and self-regulated.