Background: Recruiting and retaining faculty to teach courses is crucial for online nursing programs to succeed. The purpose of this study was to gain a fuller understanding of the benefits and challenges of teaching nursing courses online by exploring the perspectives of faculty, administrators, and instructional designers at three schools of nursing in the southeastern United States. Method: This qualitative multiple case study explored perspectives of 21 participants from different stakeholder groups. Researchers used cross-case analysis and determined emerging themes in data collected from interviews, course demonstrations, and course documents. Results: Data analysis revealed themes regarding benefits and challenges for nursing instructors in (a) teaching strategies, (b) instructor availability, (c) training and support, and (d) institutional issues. Conclusion: This study found gaps in perspectives between participant groups that indicated a need for institutions to address communication issues, training program objectives, and institutional policies and procedures regarding online course design and delivery to promote faculty success and satisfaction.