This qualitative study explored the perceived psychological impact of repeated failures on a high school exit examination (HSEE). We interviewed eight self-identified English language learners (ELLs), whose ages ranged from 20 to 29. All participants were attending tutoring HSEE programs at urban community colleges in New England. Using a modified grounded theory approach (Goldkuhl and Cronholm in "Int J Qual Methods" 9:187-205, 2010), interviews were transcribed, coded, and analyzed. The interviewees perceived many more negative effects than benefits of failing a HSEE. They reported adverse effects on academic motivation, emotions, goals, and self-perceptions. Despite these perceived adverse effects, they identified both individual (efforts, goals, self-reflection and positive mindset, positive self-perceptions) and environmental protective factors (encouragement, instructional support and emotional support) that helped them persist in attempting to pass the HSEE. The findings from study have implications for educational and psychological research, policy and practice.