There are many factors which contribute to college/university retention rates, two of which are a sense of entitlement and a lack of academic coping skills among rising college freshmen. The theoretical foundations of this research is conflict theory in education and social construct theory. This study examines grade inflation and social promotion experienced by the students in their K12 career as possible causes for such behavior. In an attempt to better understand whether or not these two practices may be catalysts in retention rate issues a qualitative multi-descriptive case study was conducted which reached out to 11[superscript th] and 12[superscript th] teachers asking if they perceived a solution to grade inflation and social promotion in relation to the behaviors of entitlement and a lack of academic coping skills. This study used two methods of data collection being both a questionnaire and Zoom® interview. Teachers who participated in the questionnaire were asked specifically if they perceived a solution the two practices of grade inflation and social promotion. The interviewed teachers were asked if they witnessed the sense of entitlement and the lack of academic coping skills in their students and if they perceived a connection between those behaviors and college retention rates. Some teachers did participate in both data collection methods thus providing some well-rounded data. Considerations for future research provided. [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.]