Course management software enables faculty members to learn one software package for web-based curriculum, assessment, synchronous and asynchronous discussions, collaborative work, multimedia and interactive resource development. There are as many as 109 different course management software packages on the market and several studies have evaluated and compared various aspects of these tools. However, these studies generally focused on checklists of what these products can do, not what these products need to do, or can do well. In addition, there is little data to suggest that the pages created by these software packages were easy to use by the students, or that the use of these tools by faculty increased the quality of instruction experienced by the students. Faculty and students have very different requirements for this one product, faculty need to be able to develop resources quickly and efficiently using this software, while students need to be able to find and access the course materials their instructor has assigned. Therefore, these analyses may be of limited predictive power in determining the applicability of different course management software for deployment by educational institutions. The objective of this study was to evaluate the usability and usefulness of course management software to support traditional classroom instruction from both the faculty and student perspective. This study was done in two parts, the first part asked participants with no experience using course management software to evaluate several packages and choose the one they preferred, and the second part was a follow-up analysis after both faculty and students had used the software for an entire semester. Faculty members and cadets found that course management software (CMS) provided a satisfactory mechanism for web-enabled curriculum delivery to supplement traditional classroom instruction at USAFA. If we had only focused on checklists of what the software products could do, then Blackboard CourseInfo and WebCT would have been considered equal, and Intralearn would have been a distant third. However, Blackboard CourseInfo received higher scores than the other products when ratings were based on user analysis of ease of use and usefulness. Many of the features found in these products such as discussion groups, student web pages and collaborative work areas that contributed to their high number of features were not widely used, nor deemed important by both faculty and cadets. Although some faculty may use these features in the future (and subsequently cadets will use them) as they become more comfortable and familiar with the software and pedagogy, at this time a CMS with an easy to use interface that contains a grade book, automated quizzes and a place to put announcements and course documents should be preferred to one that contains many collaboration features yet also has a difficult navigational interface or hard to use development tools. Many faculty members chose to use Blackboard CourseInfo for a follow on semester for a more in-depth analysis. Although faculty found CourseInfo served most of their needs, many indicated that it lacked some key features necessary for deployment at USAFA, for example there was no way to divide grade books, announcements or documents into multiple sections of the same course without duplicating the entire course. Similarly, it was not possible to share calendars, quiz questions, handouts, or content among instructors teaching the same course. Therefore, this software seems best suited for providing web-enabled instructional support to a faculty member who is teaching one section of a single course, and who does not share large amounts of content with instructors teaching other sections. As predicted, the faculty and cadets had different requirements of the CMS product for developing and accessing resources, respectively. Therefore, if only the faculty's requirements are considered, or if the product is not evaluated by all of the user groups, the probability of purchasing a sub-optimal product for a majority of the users increases. Although the requirements as stated by the faculty and cadets who had been using a CMS for an entire semester were more similar than those gathered from the naive users, often enterprise CMS purchase decisions are made prior to the purchasing of any system. The results obtained in this part of the study will help us determine the requirements for procuring a course management software system for use here at USAFA. Giving faculty an efficient means of entering their homework assignments into a database system is the first and probably most important step to achieving the vision of an integrated portal system that includes the resources the cadets need most, access to homework and reading assignments, course materials and the ability to monitor their progress through checking their grades.