“The most important aspect in the learning to teach process is the field experience, i.e., the opportunity to stand face to face with the challenges and demands of the teaching profession (Caires & Almeida, 2007).” This study represents a qualitative analysis of the successes and challenges encountered by preservice teachers while conducting a semester long student teaching practicum. Anonymous questionnaires distributed to former preservice teachers identify challenges regarding classroom management, cooperating teacher interactions and university demands. Individual case-studies of four former preservice teachers reveal a more in-depth perspective of the field teaching experiences and help uncover challenges associated with classroom management and implementing university teaching, as well as provides the foundation for establishing relevant prevention strategies for teacher education programs, university supervisors, cooperating teachers, first-year teachers and future student teachers. *Peer Reviewed Paper Published in NTEJ (see http://works.bepress.com/leah_nillas/25/)