The purpose of this exploratory case study was to examine how student-to-teacher interactions encourage students to develop self-regulated learning (SRL) habits and skills. Zimmerman's social cognitive theory of SRL, which supposes a relationship between academic success and SRL, is used as a conceptual framework. The representative case is a computer-based alternative education program for students at risk of dropping out of high school in grades 10-12. The teachers worked one-on-one with students in a computer lab while the students engaged in mastery-based learning using Apex Learning Inc. digital curriculum. Five teachers responded to three questionnaires to examine how student-to-teacher interactions influenced student-to-content interactions, and students' forethought, performance, and evaluation behavior. The teachers also submitted instructional artifacts and described instructional tools, activity types, and scaffolds within the digital curriculum. After analysis of primary and secondary data, the results showed the following: Student-to-teacher interactions encouraged students to engage in forethought behaviors associated with goal setting and strategic planning; examples of performance behaviors were using the content to increase understanding, navigating the content efficiently and effectively, monitoring the use of task strategies, and developing thinking steps; and examples of evaluative behaviors were calibrating and making accurate self-judgments. The study can promote social change by helping students at-risk of dropping out of school develop SRL strategies correlated to academic achievement and high school graduation. SRL habits are transferable to everyday behaviors associated with continued employment, maintaining healthy relationships, and lifelong learning.