Contemporary educational and social systems are increasingly confronted with complex, ill-structured problems that demand more than routine knowledge reproduction. In response to these challenges, this paper explores how contextualized critical thinking can be cultivated through Puzzle-Based Instruction (PBI) as an integrative pedagogical approach across educational and social systems. Drawing on interdisciplinary perspectives from education, cognitive science, and social learning theory, the study conceptualizes learning as an active, meaning-making process situated within real-world contexts rather than isolated academic tasks. Puzzle-Based Instruction is framed as a learning design that engages learners in carefully structured cognitive challenges, encouraging inquiry, hypothesis testing, collaboration, and reflective reasoning. By embedding puzzles within authentic social and educational contexts, PBI supports the development of transferable problem-solving skills and adaptive thinking required in rapidly changing environments. The paper adopts a conceptual and analytical approach, synthesizing existing literature and illustrative practices to demonstrate how contextualized puzzles can bridge theory and practice, foster learner agency, and promote deeper cognitive engagement. Particular attention is given to how PBI aligns with system-level goals such as interdisciplinary integration, social relevance, and sustainable learning outcomes. The discussion highlights the potential of Puzzle-Based Instruction to move beyond content mastery toward the cultivation of critical awareness, flexibility, and real-world problem-solving capacity. The paper concludes by arguing that integrating contextualized critical thinking through PuzzleBased Instruction offers a viable pathway for transforming educational and social systems, preparing learners to navigate complexity, uncertainty, and interconnected global challenges.