Although studies claim increases in underrepresented populations choosing STEM majors, barriers to retention, and higher education degree completion in STEM still exist. This study examined efforts of a prominent technical university to attract and retain urban high school graduates through a tuition scholarship program. We sought to determine the trajectories of recruited urban high school graduates and explored students reasoning behind their choice of STEM majors. Findings revealed unforeseen obstacles prohibiting students from pursuing STEM degrees despite free tuition and other benefits of the diversity recruitment program. Student obstacles included: (i) logistic barriers; (ii) academic resources access; and (iii) social/cultural support. A secondary but related finding was the self-realization of engineering faculty culpability in the attrition they observed. This critical account of race and privilege told by insiders to the engineering discipline speaks directly to the failure of educational institutions to address essential components of the economic and academic segregation which currently exists against a backdrop of reform calls which aim to diversify the engineering workforce. Implications for future research and recruitment efforts are discussed. # 2017 Wiley Periodicals, Inc. J Res Sci Teach 9999:XX-XX, 2017 Keywords: at-risk-students; opportunity gaps; critical race theory; engineering education; privilege; STEM major selection; urban education; assessment driven instruction; equity and diversity; ethnography In response to concerns the United States is losing ground in technical and innovation capabilities (National Science Board, 2014), there have been numerous calls to action to strengthen the STEM pipeline by enrolling and graduating more students from university programs in STEM. In 2004 alone, "Thirteen federal civilian agencies spent approximately $2.8 billion . . . to increase the numbers of students in STEM Fields and employees in STEM occupations and to improve related educational programs" (Ashby, 2006, p. ii). By increasing the number of individuals entering STEM fields, the goal of these measures is to support U.S. efforts to ". . . continue to innovate, lead, and create jobs of the future" (NGSS Lead States, 2013, p. 1). With predictions that by 2018 the growth rate of many science and engineering occupations will be faster than average (National Science Board, 2010), failure to strengthen the STEM pipeline could potentially erode the U.S.'s ability to remain competitive in a global economy. Engineering education reform documents continue to call for diversifying the ranks of engineers, yet the complexion of the engineering workforce has remained relatively static in its representation, expanding its non-White male membership from 9% to only 13% in over three decades (Landivar, 2013). As many studies reveal (Brandt, 2008;Brown et al