Field education is social work’s signature pedagogy, the essential preparation for professional practice. Its success depends on field educators—field instructors, task supervisors or preceptors, and faculty field liaisons—to guide and assess student learning and maintain the pedagogical integrity of the field experience. Despite its importance and complexity, few resources exist for orienting and preparing field educators.This anthology presents decision cases that depict the actual experiences of social work field educators and students. They showcase the complex dynamics of field education and highlight a range of dilemmas experienced by novice and seasoned field educators. In various combinations, the dilemmas include interpersonal boundaries, emotional reactivity, initiative, expectations, role confusion, inadequate performance, accountability, interpersonal conflict, personal values, and impairment. The cases show how other field educators have navigated the issues that typically arise, with greater or lesser success. The cases portray the intricacy and rewards of this educational role and are selected for their ability to facilitate in-depth discussion among field educators during their initial training or continuing education. Guided discussions of these cases can bolster supervisory competence and confidence. They enable field educators to develop important problem-solving and critical-thinking skills related to their overlapping roles as instructors, supervisors, mentors, advisors, colleagues, and role models, helping them thrive and continue to serve the profession.An accompanying instructor manual provides extensive information for each decision case and also includes guidance for field directors on how to use the case method of teaching and sources for additional information.