This chapter starts by answering the question, “What is critical thinking?” As it turns out, not everyone agrees on what critical thinking is. Nevertheless, researchers agree that critical thinking allows many people to reason together for solutions to complex problems. Also, in this chapter, the authors look at how computing capabilities enhance Socratic problem solving. A computer-based Socratic problem-solving system can keep problem solvers on track, document the outcome of a problem-solving session, and share those results with participants and a larger audience. In addition, Socrates DigitalTM can also help problem solvers combine evidence about their quality of reasoning for individual problem-solving steps and the overall confidence level for the solution.