The Internet has provided an ideal environment for engineering education. This thesis describes the development of a new problem generator used in the Engineering Design Tutor (EDT) system to provide multi-step problem generation capability. The EDT system allows the user to specify a set of design concepts from a specific domain, based on which a problem tree is generated. All the possible solution paths in the tree are searched and the most complete and correct path is automatically selected as the shortest path. Using the values obtained from a constraint satisfaction solution for the variables in the shortest path, and the templates provided for the problem description, the system allows the automatic generation of a set of problems all using the same shortest solution path.