Discovering information on the Web relies on the publishers of that information to describe it in a meaningful way, often at the syntactical level. Despite ongoing efforts to improve Web page description, search retrieval is more time consuming than it should be. Essentially this arises because search engines lack the capacity to identify the purpose of the search. The goal of this paper is to identify the extent to which this issue can be addressed and how the Pragmatic Web may assist in this endeavour. The paper uses Stamper's Semiotic Ladder to distinguish between those issues that are truly semantic, pragmatic or even social, versus those which are syntactic. This enables the core issues to be discovered, thereby distinguishing the areas that the Pragmatic Web community can focus upon.