This chapter provides an overview of a novel computer-based learning environment, the Diagnostic Assessment and Achievement of College Success (DAACS), designed to generate and leverage diagnostic assessment data about college students' academic and self-regulated learning (SRL) skills to create effective success pathways for students as they transition to college life. As implemented across multiple large-scale research projects conducted in online, hybrid, and traditional brick and mortar college contexts, DAACS integrates diagnostic assessments with automated and actionable feedback, social supports (i.e., advisors), and various open educational resources (OERs), such as an SRL Lab and writing support. In this paper, we reveal two key challenges when implementing DAACS technology, specifically in relation to student SRL functioning and skills: (1) quality and level of participation among stakeholders, and (2) uptake of diagnostic data and feedback. Through illustrative examples and recommended solutions to these challenges, readers will gain insights about a few important yet thorny issues related to implementing and using SRL-enhanced technological supports in college contexts.