This chapter explores the challenges that undocumented students face as they enact their career development process, considering the theoretical perspectives and developmental processes that uniquely complicate their aspirations. The authors review the professional development challenges that undocumented students face as they make career decisions and preparations. In addition, they discuss the obstacles these students encounter as their career goals are implemented, they apply for graduate and professional degree programs, or they seek full-time employment in their chosen fields. They also examine the issues that are more intrapersonal in nature, especially those related to the emotional toll on undocumented students due to the barrage of hurdles they may encounter. They conclude with recommendations to improve practice in career development centers so that staff can prepare undocumented students to achieve their educational and career goals.