The undergraduate course, Design of Machine Elements has been offered by the University of Connecticut’s Mechanical Engineering Department for many years. It has been one of the most difficult courses for students to follow and understand, and also for the faculty to teach. A strong basic knowledge of mathematics, theoretical mechanics and the mechanics of materials is required for students to take this mandatory course and to fully follow its contents. To understand entirely the concepts of Design of Machine Elements, students should be acquainted with the history of the strength of materials. Being aware of the importance of such a course the ME faculty has worked to establish outstanding structural engineering teaching and research methods, and to create a departmental nucleus of intensive development of engineering mechanics research and development. The efforts described in this paper have facilitated the teaching and learning of the mechanics of materials and consequently the Design of Machine Elements as well. To accomplish these in both teaching and practical problem solving the instructor must use the unconventional approaches and students must put a great deal of effort into learning the material. It is important for students to have a general knowledge of mathematics and theoretical mechanics, but as this is a foundation of the course, the instructor should review and clarify the specific assumptions of engineering mechanics and strength of materials. One of the pedagogical challenges to be overcome, which is faced by both instructors and students, has always been to connecting the basic theorems and application procedures of engineering mechanics to their practical use in designing machine elements and in calculating static and dynamic stresses and deformations. The concept of avoiding stress concentrations by properly designing the shapes of machine frames and parts should also be emphasized. Transforming plane stresses and deformations into three-dimensional representations and calculations should also be considered. Since machine elements are usually in motion, a dynamic approach to stress and deflection analysis is important as well. After introducing the analysis of dynamic stresses and deformations, the instructor should cover the concept of fatigue, which is the next crucial step. The instructors’ approaches and the unconventional methods they use to familiarize students with such complicated concepts are discussed in this paper. An analysis of representations of stresses and deformations and fatigue analyses of different machine elements are also considered. This paper connects to some approaches previously presented in earlier papers as well as in courses, books and discussions by outstanding engineering mechanics theoreticians, including UConn faculty, especially Dr. Roman Solecki. The paper concludes by recommending effective teaching approaches to complicated machine design concepts and summarizing the lessons learned. This paper is a companion piece to the IMECE 2015 50776 [1].