This paper examines Quine’s web of belief metaphor and its role in his various responses to conventionalism. Distinguishing between two versions of conventionalism, one based on the under-determination of theory, the other associated with a linguistic account of necessary truth, I show how Quine plays the two versions of conventionalism against each other. Some of Quine’s reservations about conventionalism are traced back to his 1934 lectures on Carnap. Although these lectures appear to endorse Carnap’s conventionalism, in exposing Carnap’s failure to provide an explanatory account of analytic truth, they in fact anticipate Quine’s later critique of conventionalism. I further argue that Quine eventually deconstructs both his own metaphor and the thesis of under-determination it serves to illustrate. This enables him to hold onto under-determination, but at the cost of depleting it of any real epistemic significance. Lastly, I explore the implications of this deconstruction for Quine’s indeterminacy of translation thesis.