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Web-based homework management systems offer students 24/7 access to problem-solving exercises and review of assignments. Is the advantage of using such systems and does it matter whether students are given one attempt or multiple attempts to solve problem? In other words, does the design of the assignments affect students’ preparedness and learning? The authors’ examine the effect of the design of online homework on student preparedness, problem solving skills, and exam performance. Data was collected from McGraw-Hill Connect, to construct the measurements to proxy for student preparedness and problem solving skills. The preliminary empirical results indicate that the design of online reading and problem homework assignments are related to exam performance and reading online assignments. In addition, it appears that exam performance is mediated by problem solving skills. Our findings suggest the design of online assignments is important in enhancing students’ problem solving skills and in motivating and engaging students in the learning process.