A graduate level course on security vulnerability assessments, including practical experience at commercial firms, has become a cornerstone of our Information Assurance curriculum. The hands on nature of the course, designing, performing and experiencing an actual team based security assessment significantly deepens the level of understanding for students. Blending academic and training aspects yields a course with significant content and a unique opportunity based delivery mechanism while at the same time providing favorable exposure of the program to the community. The development of the course has been a journey through many challenges most of which are resolved through adequate pre-class preparations. Feedback from students has shown the long term value of a true comprehensive applied course.