Despite efforts to place students on a guided pathway to successful completion, nearly one in five students who do not persist at community colleges complete 75% or more of the credit threshold for a degree before leaving the institution (Johnstone, 2018). In Texas, according to the Texas Higher Education Coordinating Board Members (THECB, 2020), 28% of community college students graduate with an associate degree, bachelor's degree, or certificate within three years. At Chaparral Community College, the percentage is even less, at 24% (THECB, 2020). This evidence points to a need for retention reform, focusing on sophomore students. This quantitative study used two pillars of the Guided Pathways model, helping students stay on the path and ensuring students are learning, as a framework for analysis. The study employed a complex approach to broaden the definition of academic integration (Tinto, 1993) by including experiences beyond the classroom resulting from enrollment in courses (Latz, 2015). By taking a complex perspective, the study used differentiated coaching as an approach to accomplish academic integration in and out of the classroom. Two logistic regression models were used to examine the differentiated coaching approach deployed through student success programming as a predictor of retention (N = 1050), semester one to semester two and semester one to semester three. Initiatives aimed at retention that involve cross-institutional reform are challenging to evaluate and often take years to observe improvements (Bailey et al., 2015). This study demonstrated this struggle as the treatment, although positively sloped, did not have a statistically significant relationship to retention in the transition from the first semester to the second. However, when students moved along their pathway to the third semester, the differentiated coaching treatment had a positive and significant relationship to retention. Therefore, there was an increased probability of being retained for students who received differentiated coaching. This upward trend is expected to continue as the advisors develop their expertise in differentiated coaching and the application to students' individual experiences. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]