<p>Following Kant’s view of drawing or shape as the “proper object” of aesthetic judgments in architecture, I present an interpretation of a central concept in his theory of aesthetic judgment, viz<i>.</i>, the <i>free play</i> of imagination and understanding, as visual calculating in shape grammars. Calculating with identity rules formalizes Kant’s reflective judgments in free play, which he explains as imagination sustaining a “lively engagement” with form. This interpretation departs from determining judgments, which underlie twentieth-century mathematical and computational approaches to aesthetics. With this interpretation in place, I address a central issue concerning computation and aesthetic intelligence, engaging Kant’s concept of “adherent beauty”: How are we to employ computation as a practical method for value judgment while preserving free play’s reflective property that refreshes aesthetic experience, especially when creative work must meet defined functions and end-goals?</p>