Many students who struggle with basic mathematics courses benefit from digital instructional technologies, including additional visual and supplemental materials on difficult concepts and skills. Currently, the intelligent tutoring technology feature in the learning management system (LMS) should make it easier for students to deal with material that is difficult for them by offering a focused and manageable way to get extra support. An intelligent tutor facilitates creation of supplemental materials and alerts both students and the instructor when performance on math assignments and quizzes falls below a predetermined threshold. In this article, the author discusses how intelligent tutoring technology can help math-challenged students. He describes his experience in using MyWebStudyTutor application for two different courses: (1) Fundamentals of Mathematics; and (2) Basic Algebra. In his trial of the MyWebStudyTutor technology, the author made a few mistakes, but when he asked for help, he realized that the mistakes were easily corrected. He benefited from two sessions with a trainer, who walked him through the procedures. In general, the instructor needs to be able to determine when a student misunderstands the concepts, and then create a rule to release additional materials with MyWebStudyTutor. The author offers some piece of advice to other instructors beginning to work with an intelligent online tutor. (Contains 7 figures and 1 endnote.)