In recent years, software operating skills, the ability in computer literacy to solve problems using specific software, has become much more important. A great deal of research has also proven that students' software operating skills can be efficiently improved by practicing customized virtual and simulated examinations. However, constructing these simulation-based examinations is cost intensive and time-consuming. Thus, a reconfigurable simulation-based test system designed on a proposed Software Operation-Finite State Machine has been developed. Using this system, teachers can use a graphic authoring tool to construct and reconfigure simulation-based tests for designated software operation tasks. For the students, these simulation-based tests can be performed via the Web browser without any extra computer environment setting costs. After students finish the test, the proposed system can automatically assess their online operating paths to generate the assessment report for self-reflection. Moreover, in order to share and reuse the designed simulation-based tests, this paper suggests some extensions of IMS Question & Test Interoperability to support the proposed simulation-based operation test format. Finally, an experiment was conducted to evaluate 38 sixth grade elementary school students. The experimental results show that this system can meet both teachers' and students' educational requirements while significantly improving students' learning performance of the software operating skills.