As technology in education continues to improve, research is necessary to assess the impact it is having on students’ confidence in the way students solve mathematics problems. The purpose of this quasi-experimental, non-equivalent control-group comparison study is to examine the impact the Desmos graphing calculator has on the problem-solving confidence of middle school and high school students as compared to students who use a TI-83 Plus graphing calculator while controlling for students’ math achievement scores. The students (N = 146) participating in this study were learning their respective mathematics material for an equivalent period of 12 weeks in order to determine whether students who used the Desmos calculator experienced a statistically significant difference in problem-solving confidence levels. Students in both groups took the assessment at the end of the 12-week period of learning and an Analysis of Covariance (ANCOVA) was used to test whether there was a significant difference in the scores of the Problem Solving Inventory (PSI). Results indicate that there was a statistically significant difference in problem-solving confidence scores between middle and high school students who used the Desmos graphing calculator as compared to students who used a TI-83 Plus graphing calculator, while controlling for student math achievement scores.