Maple T.A. is a Web-based system for creating tests and assignments, and automatically assessing student responses and performance. It supports complex, free-form entry of mathematical equations and intelligent evaluation of responses, making it ideal for science, technology, engineering, mathematics (STEM), or any course that requires mathematics. Adaptive questions provide a tool to improve student comprehension, providing extra guidance to students who give an incorrect response to a question, increasing their understanding of the concepts and techniques involved. The system also features a highly secure Proctored Browser, which reduces cheating by ensuring students stay inside the Maple T.A. environment until the test or assignment is completed.