An enterprise is a complex sociotechnical system, purposefully designed for a certain service, which is realized through the business of the enterprise. The enterprise service is delivered to its customers in a certain business environment, which is often dynamic and changing. The already complex business operation (business processes) of modern enterprises are further challenged by the dynamicity posed by the enterprise business environment. For tackling this enterprise complexity (analysis and design), modeling and simulation have shown great potential. Modeling in enterprise study, especially during the analysis and design phases, plays crucial role as it represents a design artifact in a more visualized manner such as intuitive diagrams. This e-book, contains papers covering a broader application of modeling and simulation in the enterprise context. The papers show the diversity of application potential for enterprise modeling and simulation ranging from re-engineering to organizational aspects, technology alignment, and domain specific type of enterprise.