This paper describes experiences in organizing and running an internship component of an undergraduate program in information systems security. In 2004, Sheridan College Institute of Technology and Advanced Learning introduced a novel Bachelor in Applied Information Sciences (Information Systems Security) program. The intent was to educate well-rounded specialists in the field and provide them with valuable work experience during the 8-month long co-op term. The research presented here is based on the co-op officer reports, statistics reported by the co-op office, interviews with the students and other anecdotal data mainly collected through conversations with the involved parties. Besides providing facts that speak to the quality of the program and appropriate organization of the job placements, the authors critically examine successes and challenges encountered in this process. Comparison with other information systems security postsecondary programs in Ontario, Canada, is given based on type of program, characteristics and focus of curriculum content and length of internship.