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The advent of affordable high performance computing (HPC) resources, such as computing clusters and grids, has transformed the computational capabilities of many organizations. However, the lack of convenient interfaces to such valuable resources limits their effectiveness, restricting their user base to a small set of highly skilled programmers and computer scientists. Without such an interface, domain specialists lacking exceptional knowledge of HPC systems are challenged in their ability to utilize these computing grids. This paper describes the design and implementation of a Web-based user interface aimed at increasing the usability and transparency of a 341-node computing cluster to multiple applications and user communities, by developing a streamlined Web interface. In discussion of the design, we address several common concerns including security, extensibility, and maintainability. We also outline two distinct solutions to this problem: our earliest approach using open-source grid computing tools such as the Globus Toolkit and Gridportlets, and our most current implementation, which uses a prototype Python-based Web application developed as a part of this paper. We then assess our experience with both approaches and conceptually evaluate them based on the common concerns mentioned above. Finally, we argue that, despite the flexibility afforded by the industrial-strength grid tools, a simpler, home-grown approach similar to our Python-based prototype is most effective in terms of time and maintainability for enterprises seeking to develop similar Web-based front ends for their computing resources. We conclude that our approach provides better value to a set of users as it increases in both number and diversity.