Currently, more than half the library staff at a medium-size academic library maintain large numbers of static Web pages using Web editors, rather than content management tools. While not optimal in the technical sense, this process does maximize the individual’s creative contributions to the site. Because of this flexibility, feedback about this process has been primarily positive at an individual level. However, a growing number of challenges in the areas of content, priorities, technical skills, and workflow exceptions have cast doubt on this system’s long-term prospects. This chapter discusses the balance between individual and group needs, and the true cost of a purely technical solution to the problem of Web maintenance.