In this paper, we analyze medical searching behavior performed by a typical medical searcher. We broadly classify a typical medical searcher as: non-medical professionals or medical professionals. We use behavioral signals to study how task difficulty affects medical searching behavior. Using simulated scenarios, we gathered data from an exploratory survey of 180 search sessions performed by 60 participants. Our research study provides a deep understanding of how task difficulty affects medical search behavior. Non-medical professionals and medical professionals demonstrate similar search behavior when searching on an easy task. Longer queries, more time and more incomplete search sessions are observed for an easy task. However, they demonstrate different results evaluation behavior based on task difficulty.