In this paper we introduce the iWatch web crawler, a tool designed to catalogue and analyze online data practices and the use of privacy related indicators and technologies. Our goal in developing iWatch was to make possible a new type of analysis of trends, the impact of legislation on practices, and geographic and social differences online. In this paper we present preliminary findings from two sets of data collected 15 months apart and analyzed with this tool. Our combined samples included more than 240,000 pages from over 24,000 domains and 47 different countries. In addition to providing useful and needed data on the state of online data practices, we show that iWatch is a promising approach to the study of the web ecosystem.