In this chapter, I first examine two metaphors – the astral and the entomological – that extend through Nietzsche’s entire corpus to track the development of certain key themes in Nietzsche’s metaphilosophical reflections as they evolved from the early days of his professorship at Basel up to the mature writings of 1886 and 1887. By then, I argue, Nietzsche’s metaphilosophical meditations had crystallized around his critique of the so-called will to truth. I then argue that key to this critique is Nietzsche’s conviction that philosophical “knowledge” is not just different in kind to the type of knowledge produced by scholars and scientists, but that the two have contrary properties. Finally, I make use of these results to mount a Nietzschean metaphilosophical critique of the now prominent analytical reception of Nietzsche. A sizable share of contemporary English-language philosophical work on Nietzsche, I argue, is not just metaphilosophically discontinuous with Nietzsche’s understanding of and approach to philosophy, but expressive of deep-set resistance to precisely those transformations in philosophy that Nietzsche sought to bring about as an engaged metaphilosopher.