How do we know how?

I raise some doubts about the plausibility of Stanley and Williamson's view that all knowledge-how is just a species of propositional knowledge. By tackling the question of what is involved in entertaining a proposition, I try to show that Stanley and Williamson's position leads to an uncomfortable dilemma. Depending on how we understand the notion of contemplating a proposition, either intuitively central cases of knowing-how cannot be thus classified or we lose our grip on the very idea of propositional knowledge, which then fails to demarcate any clear class of cases. I conclude with a brief discussion of the nature and role of knowledge-how, and its relation to the important, but less explored, notion of expertise.