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This paper will study two photographic series by Pablo Delano (San Juan, 1954) that focus on Hartford and Santurce (Hartford Seen, Connecticut Historical Society, 2013-2015; “PR Urban Art I and II,” 2014-2015) and display creative responses Puerto Ricans and other racialized Caribbean people to precarity, a “politically induced position in which certain populations . . . become differentially exposed to injury, violence, and death” (Butler, Frames of War 25). Fixing on the built environments of Hartford—a city of 41,995 Puerto Ricans and large numbers of other Caribbean people—, Delano captures the city’s transnational dynamics and creative endurance of racialized communities. When shooting Santurce—a working-class city with significant return migration from the US and other Caribbean residents—, the artist captures public art spurred by the anti-gentrification, artistic initiative, “Santurce es ley.” I argue that Delano’s Hartford and Santurce photographs avoid direct representation of faces, while metaphorically encoding the facial trope. By deploying parataxis and framing, and inscribing micro-details in pictures, these images foster a delayed intersubjective identification with the subjects of photography and incite a nuanced and intellectual engagement with the geopolitical entanglements that produce precarity in these Puerto Rican and Caribbean cities.