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The distribution of commands issued by experienced users of a computer operating system allowing command customization tends to conform to Zipf's law. This result documents the emergence of a statistical property of natural language as users master an artificial language. Analysis of Zipf's law by Mandelbrot and Cherry shows that its emergence in the computer interaction of experienced users may be interpreted as evidence that these users optimize their encoding of commands. Accordingly, the extent to which users of a command language exhibit Zipf's law can provide a metric of the naturalness and efficiency with which that language is used.