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Understand is a word frequently used in daily life, it is also an important philosophical concept. It may seem to be simple, but careful analysis, we would find there are more problems than we think. In the later Wittgenstein's Philosophy, it is one of several concepts at the core. In Wittgenstein's view, the understanding plays an important role in life and practice. The Chinese Room Argument, I will explain later, why the both sides of argument will focus on the point "What is understanding". The Turing Test, it seems to don't matter with "understanding" in the surface, and it itself is trying to avoid defining this concept, but because the real targets of the Chinese Room argument is the Turing Test, it also involuntarily involved. Thus, understand become the best clues that used for compared these three.First, this article will be in-depth analysis of these three. To clarify these three issues on the basis of their own, we use "understand" as the main thread, and do a brief comparative analysis, trying to draw some useful views. The key point of Turing Test is "can't tell very well"; Turing test is a high fair test. Mystery of the Chinese Room Argument lies in its use of our intuition, but his argument is certainly flawed. The understanding, in Wittgenstein's view, is a relatively vague concept. It is not experience, it does not mean marker, and it is not a process, while it is not a mental state or the brain of disposition. It has some differences and connects with "explain", "knowing" and "ability".And then, from the view of" the nature of understanding in its usage", I try on give out the own view on the Turing Test and the Chinese Room Argument, and stress the important role of life and practice. Finally, I would point out the Wittgenstein's philosophy is very meaningful even in our day as before.