Chinese Chan or Zen Buddhism is renowned for its improvisational, atypical, and perplexing use of words. In particular, the tradition’s encounter dialogues, which took place between Chan masters and their interlocutors, abound in puzzling, astonishing, and paradoxical ways of speaking. In this chapter, we are concerned with Chan’s use of paradoxical language. In philosophical parlance, a linguistic paradox comprises the confluence of opposite or incongruent concepts in a way that runs counter to our common sense and ordinary rational thinking. One naturally wonders about Chan masters’ rationales for their use of paradox. There are also concerns about whether the use violates the logical principle of noncontradiction to the effect that nothing can be both P and not-P all over in the same way at the same time. Chan became a viable Chinese Buddhist tradition during the Tang dynasty (618−907) and continued to develop for several centuries. The tradition had produced a huge literature; consequently, our investigation of its use of paradox cannot but be limited and selective. In the second section, I first sketch key ideas of Chan that are pertinent to our investigation and then examine the use of paradox in the sermons associated with certain Tang masters of the southern Chan. In the third section, I analyze the presence of paradoxical language in post-Tang encounter dialogues. The fourth section concludes.