This ethnographic study examines North American Jewish immigration to Israel through the lens of Nefesh B'Nefesh (NBN), a private organization facilitating aliyah since 2001. Through participant observation aboard a charter flight from JFK to Tel Aviv and interviews with recent immigrants, this research explores the motivations, experiences, and challenges of contemporary North American olim. The methodology includes in-flight observations of 225 immigrants from 19 states and 3 Canadian provinces, as well as ground-based interviews in Jerusalem with NBN participants and members of Tnuat Am, an earlier grassroots aliyah movement. Findings reveal that NBN has successfully increased North American aliyah rates by 20 percent through comprehensive support services including financial assistance, employment networking, and social integration programs, with 93 percent of NBN olim achieving employment. However, the study identifies significant challenges including economic precariousness, cultural adjustment difficulties lasting up to ten years, and the complex negotiation of American-Israeli hyphenated identity. Conservative Jewish immigrants face particular challenges in articulating their religious identity within Israel's binary religious framework. The research concludes that while NBN has transformed the aliyah experience through American pragmatic approaches, long-term success depends on immigrants' ability to navigate the sustained tension between American values and Israeli realities.