The purpose of this study was to evaluate high school students' performance in analyzing complex arguments with the support of an off-the-shelf argument mapping software, Rationale™, which provides diagramming tools with guided prompts. This study attempts to: (1) evaluate the quality of student's argument maps in terms of structural characteristics that equate to specific critical thinking skills measured in the Cornell Critical Thinking Test (CCTT); and (2) test for correlations between specific qualities observed in students' argument maps and their critical thinking skills measured with the CCTT. The results show that students can use argument maps to identify and analyze claims and arguments, but the quality of their analysis varies. This highlights the potential of the CAAM tool for enhancing critical thinking skills and text comprehension, but there are limitations. The weak correlation between CCTT and CAAM scores suggests that CCTT questions may not fully assess the skills needed for in-depth argument analysis. The study offers insights for future research and suggests new directions for exploring the relationship between CCTT and CAAM. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]