The use of podcasting technology in language learning presents a unique set of challenges and holds a great deal of promise for digital natives as well as for newcomers to technology. The literature on podcasts in learning mainly focuses on student experiences in formal educational settings, while questions related to nontraditional students in freely-available language programs provided by non-profit organizations remain unexplored. Taking a case study approach, this research examines how podcasting enhances the English learning experiences of students in an English as a Second Language (ESL) course offered by a non-profit organization that provides community services to immigrants in Canada. This chapter discusses instructional and organizational benefits as well as the challenges of applying podcasts in language training. By triangulating the experiences of the students, instructor, and program coordinators, we are able to examine the effectiveness of such a program and offer recommendations for similar programs in the future.