One common problem that occurs to students during breaks is the retrogression of knowledge due to lack of practice. This problem occurs for students at all levels of education but is especially harmful to students who are taking sequential classes such as Calculus for Engineers I and Calculus for Engineers II where the retention of topics taught in Calculus for Engineers I are required for students to succeed. One solution to this problem is the Keep in School Shape (KiSS) program. The KiSS program is a very efficient and easily accessible program that allows students to stay warmed up and ready to go when they start a sequential course by having daily review material during academic breaks. During an academic break, students who are signed up for the KiSS program are sent a link through text message or email every day that allows them to access a multiple choice review problem. The review problem that they are given is a problem that presents material from the previous course that will be needed in the upcoming course. At the beginning of the review, students have the option to choose between a Level 1 or a Level 2 problem, where a Level 2 problem is related to its Level 1 counterpart but slightly more difficult. Before the students are permitted to solve the problem, they must first use a five point scale that indicates their confidence in their ability to solve the problem. After they complete either the Level 1 or Level 2 daily problem, those that got it wrong have the option to view a hint and try again or view a solution. The students that got the Level 1 daily problem right are also allowed to view the solution but will be permitted to go onto the next level right away whereas the students that got the Level 1 problem incorrect will need to try a similar problem before being able to move onto Level 2. For students who chose to do the Level 2 problem and were not very confident, they were given the option to solve a level 1 problem instead. Students who chose level 2 and got it wrong are given the options to view a hint and try again or simply view the solution before moving on to flashcard versions of the daily problems. Students who get the Level 2 problem correct are also given the option to continue practicing using the flashcards if they choose to. Once a week, there is also a trivia day where students have the choice to complete solely a mathematical trivia question or complete both the trivia question along with a daily review problem. This feature allows students to take a day off from doing mathematics if they choose, but still stay engaged by doing a related activity. Through this program, there is a lot to learn about whether doing Level 1 problems can help students improve their understanding of a concept enough to correctly solve a Level 2 problem. There are many factors to consider such as which question the student chose to answer first, student confidence, and student perseverance. Through the Summer Break 2023 KiSS program, there was data collected for every student answer for each day they accessed the daily KiSS activity. This thesis presents an analysis of the data showing how having two levels of problems is beneficial for students and the correlation between students’ results in Level 1 problems and Level 2 problems for students who chose to attempt both problems.