A user’s single session with a Web search engine or information retrieval (IR) system may consist of seeking information on single or multiple topics, and switch between tasks or multitasking information behavior. Most Web search sessions consist of two queries of approximately two words. However, some Web search sessions consist of three or more queries. We present findings from two studies. First, a study of two-query search sessions on the AltaVista Web search engine, and second, a study of three or more query search sessions on the AltaVista Web search engine. We examine the degree of multitasking search and information task switching during these two sets of AltaVista Web search sessions. A sample of two-query and three or more query sessions were filtered from AltaVista transaction logs from 2002 and qualitatively analyzed. Sessions ranged in duration from less than a minute to a few hours. Findings include: (1) 81% of two-query sessions included multiple topics, (2) 91.3% of three or more query sessions included multiple topics, (3) there are a broad variety of topics in multitasking search sessions, and (4) three or more query sessions sometimes contained frequent topic changes. Multitasking is found to be a growing element in Web searching. This paper proposes an approach to interactive information retrieval (IR) contextually within a multitasking framework. The implications of our findings for Web design and further research are discussed.