The spotlight of this Afterword is on technologies and artifacts as tools that have a critical impact on critical thinking. An ideal critical thinker learns how to select and use these tools in the right context for the right problem at the right time. However, most students and adults do not autonomously use these tools in sensible ways and our educational systems do not offer sufficient training. This gap limits the development of critical thinking and other twenty-first-century skills. Critical thinking requires reasoning, problem solving, and deep comprehension of the material, whereas people tend to settle for shallow understanding. The first half of my career explored instructional interventions to increase the readers’ depth of comprehending texts and multimedia, such as planting contradictions in the text, inserting claims that clash with world knowledge, or requiring them to solve a problem. The second half of my career focused on developing and testing digital technologies that facilitate deeper comprehension, problem solving, reasoning, and other dimensions of critical thinking. For example, AutoTutor is an intelligent conversational agent that simulates a human tutor by holding a conversation in natural language, with speech, facial expressions, pointing, and gestures. Agent-based systems were developed to train students on self-regulated learning, evaluation of information sources, detection of misinformation, and critical thinking in science. My work with OECD (Organisation for Economic Cooperation and Development) has included digital assessments of collaborative problem solving and the role of artificial intelligence, robots, and generative AI on the future of work.