Problem-posing activities have been shown to motivate students' learning while promoting a multifaceted and interesting educational environment. Moreover, these activities enable students to be engaged in personal interpretations of their own mathematical thinking. The purpose of this study was to determine if using a handson learning intervention with multiple representations could improve students' problem-posing skills. The researchers examined the answers of the participants (n = 14) with the greatest increase in scores from pre to posttest after participating in 20 problem-posing intervention activities to determine how the intervention allowed students to pose valid, real-world semi-structured problems. The researchers qualitatively analyzed the posed problems for logical real-world contexts and the alignment of the setup of each problem to determine if the students' posed problems were logical and solvable. Results from this study confirm that students were able to build stronger understanding of mathematical content when they were engaged in authentic problem-posing activities that were meaningful to them. Thus, teachers need to include purposeful and focused problem-posing activities into their classroom lessons.