Web searchers often exhibit directed search behaviors such as navigating to a particular Website. However, in many circumstances they exhibit different behaviors that involve issuing many queries and visiting many results. In such cases, it is not clear whether the user’s rationale is to intentionally explore the results or whether they are struggling to find the information they seek. Being able to disambiguate between these types of long search sessions is important for search engines both in performing retrospective analysis to understand search success, and in developing real-time support to assist searchers. The difficulty of this challenge is amplified since many of the characteristics of exploration (e.g., multiple queries, long duration) are also observed in sessions where people are struggling. In this paper, we analyze struggling and exploring behavior in Web search using log data from a commercial search engine. We first compare and contrast search behaviors along a number dimensions, including query dynamics during the session. We then build classifiers that can accurately distinguish between exploring and struggling sessions using behavioral and topical features. Finally, we show that by considering the Struggling/exploring prediction we can more accurately predict search satisfaction.