An increasingly popular technique for decreasing user-perceived latency while browsing the Web is to optimistically pre-resolve (or prefetch) domain name resolutions. In this paper, we present a large-scale evaluation of this practice using data collected over the span of several months, and show that it leads to noticeable increases in load on name servers-with questionable caching benefits. Furthermore, to assess the impact that prefetching can have on the deployment of security extensions to DNS (DNSSEC), we use a custom-built cache simulator to perform trace-based simulations using millions of DNS requests and responses collected campuswide. We also show that the adoption of domain name prefetching raises privacy issues. Specifically, we examine how prefetching amplifies information disclosure attacks to the point where it is possible to infer the context of searches issued by clients.