Abstract Kant maintains that the only principle of the judgment of taste is the principle of aesthetic purposiveness of nature. The two central concepts of which this principle consists are free play and beautiful Form. Many interpreters complain that Kant’s concept of free play is obscure and ambiguous, and criticize that Kant can do no more than use metaphorical expressions to explicate his idea; and, as a result, they attempt to modify and supplement Kant’s idea with their own interpretations. Among those newly proposed interpretations, Paul Guyer’s so-called “meta-cognitive” interpretation is seemingly regarded as the most comprehensive and persuasive. This paper aims to immanently analyze and criticize Kant’s concept of free play so as to illuminate Kant’s “transcendental conception” of the judgment of taste, and then to argue that not only is Kant’s concept of free play coherent, it also has its modern meaning. The fundamental point of Kant’s transcendental conception is that a priori ground of the possibility of the judgment of taste is established on the basis of the features and procedure of the power of judgment. My analysis is conducted through the following four steps. First, the concept of free play is clarified and explicated by rearranging and comparing the relevant paragraphs of Kant. Second, the two fundamental assumptions of the ＊ Received October 08, 2008; revised January 14, 2009; accepted January 15, 2009. Proofreaders: Yi-Jen Tsai. Ya-Ting Yang. Thanks to the National Science Council, Taiwan, for their financial support (NSC93- 2411-H-007-016-). Because of its length, this article is published in two parts. The first part, containing the Chinese abstract, introduction and section one was published in the previous issue (No.19, February 2009). ＊＊Assistant Professor, Graduate Institute of Philosophy, National Tsing Hua University“meta-cognitive” interpretation, which Guyer attributes to Kant, are analyzed and criticized. In the first two steps, in addition to clarifying the concept of free play and explicating Kant’s underlying conception of the judgment of taste, the principal difficulties and problems about understanding Kant’s concept of free play are also pointed out. This set of difficulties and problems can be regarded as a leading thread that can be used to organize this paper’s discourse structure. Two major problems are identified from this analysis: (1) How does an aesthetic representation relate to an object? (2) How is the mutual promotion or prevention between imagination and understanding in the aesthetic mere reflection to be understood and interpreted? Third, Kant’s transcendental conception of free play and his principle of aesthetic purposiveness are explicated by comparing the similarities and differences of the procedures adopted in aesthetic “mere reflection” and “cognitive reflection” by imagination and understanding. Finally I shall succinctly explain how to apply the principle of aesthetic purposiveness to the judgment of “adherent beauty” ; the explanation aims to show that the judgment of adherent beauty is still a judgment of taste about beauty of an object, rather than a judgment about the satisfaction in the perfection; and that although the latter is also a “sensible” (aesthetic) judgment, it is no longer a judgment of taste in Kant’s sense, because it contains a concealed judgment of reason about the perfection.