Purpose: This paper aims to report on a project aimed at using simulation for improving the quality of teaching and learning modeling skills. More specifically, the project goal was to facilitate the students to acquire skills of building models of organizational structure and behavior through analysis of internal and external documents, and interviews with employees and management. An important skill that practitioners in the information systems field need to possess is the skill of modeling information systems. The main problem with acquiring modeling skills is to learn how to extract knowledge from the unstructured reality of business life. Design/Methodology/Approach: To achieve the goal, a solution was introduced in the form of a computerized environment utilizing multimedia to simulate a case of an apprenticeship situation. The paper gives an overview of the problem that the solution addresses, presents the solution and reports on the trial completed in a first-year undergraduate course at Stockholm University. Findings: The results of the trial indicate that using rich multimedia along with a case-based learning approach did improve the overall performance of the students. It was also shown that both students' and the teachers' attitudes toward the solution were positive. Originality/Value: The solution presented in this paper, using computer simulation in teaching/learning by focusing on an apprenticeship situation, can be reused by other university teachers, especially in the Information Systems discipline. This solution can thus be used in teaching, system design, requirements engineering, business analysis and other courses typical for information systems.