Since the outbreak of the Syrian Civil War in 2011, many jihadist organizations have been operating in Syria and Iraq. The two most dominant groups are the Islamic State (IS) and al-Qaeda, which have benefitted from a massive influx of foreign volunteers from all over the world. This chapter provides a statistical and qualitative analysis of the 72 American individuals who succeeded in traveling to join jihadist groups abroad. While other scholars have written about the general phenomenon of Westerners traveling to join jihadist groups as foreign fighters, no other piece includes a deep analysis of American individuals who did so. These travelers are divided into three categories: pioneers, networked travellers, and loners. Pioneers are individuals who arrived early in Syria and Iraq and ascended the leadership hierarchy quickly due to past experience in relevant skills such as military training, past participation in jihad, proficiency in religious doctrine, and propaganda production capabilities. Networked travelers are those who relied on personal contacts with fellow jihadist supporters to facilitate and plan their travel to Syria and Iraq, whether those contacts be friends, family, or individuals belonging to the same community-based cluster. Last, loners successfully traveled to Syria and Iraq without the assistance of anyone else they knew personally, yet still managed to avoid detection and apprehension.