Web-based courseware are widely developed for distance learning programs in continue education, employee training center, and e-learning portals. Usually, a Web-based courseware contains course contents and on-line tests. However, most Web document development tools are not incorporated with a strategic evaluation mechanism, to allow a quantitative analysis of distance learning courseware. We propose an evaluation mechanism and a multimedia tool, based on our Courseware Diagram, to allow a quantitative justification of courseware. Courseware produced by our development system allows an instructor to choose different instruction sequences based on the outcomes of an exam. Alternatively, the courseware may allow self-guided study in a Web-based distance learning program. This paper explains the courseware diagram, the evaluation algorithm, and the design of our courseware development system.