There is limited literature connecting the field of school counseling and pre-service counseling education programs to the individual student planning process with English learners in high school. This study employed multiple case studies to explore the issues that arise during school counselors' planning sessions with recently arrived English learners enrolling in high school. It provides an in-depth analysis of the linguistic, cultural, and social complexities of migrant English learners in a large, urban school district in North Carolina and how the participating counselors' pre-service programs prepared them to work with such student populations. The social constructivist research lens amalgamated with the American School Counselor Association (ASCA) National Model for School Counselors and the Sheltered Instruction Observation Protocol served as the conceptual framework for the study (Echevarria, Vogt, & Short, 2008; ASCA, 2005). Semi-structured interviews, ethnographic observations, and analysis of student documents solidified the qualitative research design. Constant comparative analysis inductively identified and thematically categorized the emergent data. Open axial and selective coding served to refine the identified common themes and subsequent themes. This study had four significant conclusions: (1) There is a notable gap between school counseling educational preparation and practice; (2) There is a need for expanding linguistic and cultural competencies within the profession of school counseling; (3) Specific professional development must be designed and implemented to address school counselors' linguistic and cultural competencies; (4) Pre-service counselor programs should consider including coursework to address the issues of English learners. [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/en-US/products/dissertations/individuals.shtml.]