Students regularly struggle with mathematical tasks, particularly those concerning non-routine problems in geometry. Although educators would like for their learners to transfer their knowledge to non-routine and real-life situations, students run into a number of difficulties. The goal of this exploratory study was to analyze three participants' problem solving processes in a dynamic geometry software (DGS), and therefore, gain insights about how DGS was used to support solving non-routine geometry problems. Here I viewed the DGS as a cognitive tool that can enhance and reorganize the problem solving process. The three participants were in different phases of their educational career in mathematics and/or mathematics education (bachelor, master, and doctoral student). Only one problem-the Land Boundary Problem-from the TIMSS video study will be discussed here. In this problem, the participants had to straighten a bent fence between two farmers' land so that each farmer would keep the same amount of land. All three participants solved the problem, but used the same computer-based problem-solving tool differently. While a DGS allowed and supported some participants to discover new methods of thinking, and unanticipated ways of using it, it also inhibited the problem solving processes through development of tool-dependency by some. Its different use was dependent on the presence of managerial decisions, ability to manage different resources, and problem solving experience. Based on these findings, I make recommendations for technology-embedded problem solving with an emphasis on the importance of appropriate tool use in educational settings and offer some teaching methods that may be worthwhile for research.