Post-secondary education attainment results in higher salaries (Pew Research Center, 2014) and an increase in positive societal benefits (Baum, Ma, & Payea, 2013). Nevertheless, only 31% of U.S. citizens over the age of 25 have a bachelor's degree (U.S. Census Bureau, 2014). While tradition would dictate the preparation for going to college begins in the later high school years (Gaertner & McClarty, 2015), a recent push has emerged for shifting the beginning of such conversations to middle school (Curry, Belser, & Binns, 2013; Gaertner & McClarty, 2015; Mattern, Allen, & Camara, 2016; Nemelka & Nemelka, 2016). Furthermore, advances in educational technology, such as digital badging, have allowed for new ways to deliver instruction and collect relevant data. The following study delineates a nine-week college readiness course implementation with middle school students (n = 71) from a large public Midwestern middle school with high proportions of low-income and underrepresented populations. Digital badging served as one of the principle methods for instructional delivery and evaluation. The control group (n = 20) received standardized feedback throughout the course, while the study group (n = 51) received customized instructor feedback, either through digital badging (n = 17) or in the classroom using modules (n = 34). Results suggest that after completing the course, middle school students increase their ability to articulate proper principles and strategies to implement in an effort to better prepare for future college access, are able to identify more mentors in their life to aid in future educational attainment, and find feedback helpful in the process, with various types of feedback discussed regarding the quantity and quality of curriculum scores. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]