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The debate of a thinking machine continues on, especially in an era where machines are achieving tasks that we never thought possible. In this essay, I explore one of the most famous critiques of the thinking machine, Searle’s Chinese room, by breaking down his argument into two claims of varying scope. I then offer an alternative method to assess this argument, by employing a top down approach in contrast to Searles which seems to advance from the conclusion. I explore the current thinking on how the human brain may come to understand the world, as well as some of the aspects of these semantics. This is all in an effort to elucidate some the features necessary for machine understanding and to accurately assess whether a machine possesses them. I conclude that Searle may have been too quick to judge the abilities of computers, and that a claim that any digital computer cannot understand is much too strong.