More and more, internal applications are being moved from legacy systems into a more flexible Webbased environment. The issue concerning World Wide Web technologies is important to today’s businesses. Decision making in this area is complex and needs to consider carefully the characteristics and needs of the entities employing these technologies. It has furthermore become clear that the Internet, in particular the World Wide Web, is playing an increasingly larger role in how people communicate. Through this research, technologies used to serve dynamic Web content are compared. This comparison includes performance as well as cost issues, the things that professionals in the business world face when deciding the best implementation of Web server technologies. Existing studies cover a limited scope of the overall picture, and research has thus been focused into very narrow aspects of the global entity. However, the continuing developments in Web technologies dictate the need for a broad scope approach to comparative studies in this field. Such a scope is pursued in this research.