The experiences students have as they pursue graduate degrees in Science, Technology, Engineering, and Mathematics (STEM) are governed by numerous dynamics that are at play outside the context of any classroom. The relationships students share with their peers, advisors, administration, and university significantly impacts their trajectory as scholars, professionals, and future educators. This dissertation consists of three major studies that are each focused on examining student's experience through a critical lens and characterizing their interactions with the graduate apparatus. The first two papers address socialization and well-being of engineering students and the third on how a graduate preparatory program successfully prepares students for the challenges of graduate education. All three papers used similar approaches to data collection and shared interwoven themes and theoretical frameworks in their aim to tangibly represent the sentiments shared by students. Results of these works call into question the extent to which engineering graduate programs cultivate well-being among their students, how engineering students conceptualize academia, and the impact of graduate preparation on student socialization. In each chapter, practical recommendations for departments, faculty, and students are provided along with a challenge to reflect upon existing norms and paradigms prevalent in higher education. This work provides a more complete characterization of STEM graduate education. [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.]