Critical thinking is often thought of as a generic skill trainable out of the context and transferable across different contexts. However, there are exogenous (e.g., groupthink under the pressure to conform) or endogenous factors (e.g., their self-interest taking priority over justice), that present various impeding conditions for critical thinking. This chapter looks closely at learning in academic as well as professional domains and argues that critical thinking should be treated as an integral part of learning itself, rather than an added-on feature that can be detached from learning itself. It extrapolates further that domain expertise involves critical thinking that tunes into the intricacies and uncertainties inherent in complex domains. In the age of information and the so-called post-truth world, critical thinking is being threatened not only by those who claim that, ultimately, AI will take over and human intelligence will become secondary (or irrelevant), but also by those who give up their power of mind and succumb to technocracy. If context indeed matters, it follows that the focus of teaching critical thinking should not be merely on the neat conceptions and teaching of critical thinking per se, out of context; instead, one should look into various contexts in which humans can easily lose their ability to think critically. Furthermore, critical thinking can be enhanced by developing a sensitivity to constraints and impediments imposed upon critical thinking so that not only critical thinking can be enhanced in academic and professional domains but it can become truly one’s habits of mind.