This critical qualitative study of testimonios with undocumented Latina/o students in the Midwest explored how institutional agents impacted the level of difficulty students experienced in navigating their collegiate environments. We used social capital theory and Latino critical race theory as our analytic frameworks and employed a critical race methodology to examine and deconstruct students' interactions with institutional agents. Two types of institutional agents emerged in the data: (a) unapologetically uneducated stakeholders who were not knowledgeable of ways to support undocumented or DACAmented students (and often resisted seeking out this knowledge) and (b) supportive and knowledgeable stakeholders who often independently sought out ways to assist undocumented students within institutional contexts that were often unprepared to support them systematically. Findings revealed students often encountered institutional agents who knew very little about relevant resources and policies, leading many students to feel as if they needed to educate staff and faculty.