Annotations represent an increasingly popular means for organizing, categorizing and finding resources on the social web. Yet, only a small portion of the total resources available on the web are annotated. In this paper, we describe a prototype - iTAG - for automatically annotating textual resources with human intent, a novel dimension of tagging. We investigate the extent to which the automatic analysis of human intentions in textual resources is feasible. To address this question, we present selected evidence from a study aiming to automatically annotate intent in a simplified setting, that is transcripts of speeches given by US presidential candidates in 2008.