For diasporic communities, food functions simultaneously as a cultural connection to a distant homeland and a unique entryway into the local host community. Restaurants, in particular, offer migrants and their descendants the opportunity to both reproduce past traditions and establish an entrepreneurial foothold in a new context. As more migrants join existing diasporic communities, and as new generations are born into, and interact with, the local host space, multiplicities of culinary representations emerge. In long-term diasporas, the interactions between these representations can be well observed given the variety of claims to “real” or “original” version of a particular cuisine. This notion of contending assertions of authenticity drives the central question of this article: How are authenticity and cultural identities navigated/negotiated in the diaspora by individuals with a variety of temporal and spatial connections to a physical and symbolic homeland and the local host community? I explore this question within the context of the Arab community in Chile. Chile hosts the largest population of Palestinians in diaspora outside of the Arab world, and the migratory history between the two regions exemplifies the movement of culture and ideas across immense temporal and spatial distances. This study is based on 100 hours of ethnographic observation in restaurants, grocery stores, and other food spaces in addition to 30 interviews with cooks, store owners, and local residents living in six Chilean cities during the summer of 2018. Based on this research, I argue for layered authenticities— contending that within a market for food culture, multiple claims to authenticity and attempts to authenticate cuisine are in a constant state of tension, coexistence, or harmony with one another.