This dissertation traces the contours of what I call the Cuban digital archipelago—a fragmented, transnational network of cultural production and circulation that connects Cubans within and beyond the island. In a context shaped by political censorship, infrastructural scarcity, and the steady erosion of institutional support, Cubans have turned to digital and analog tools not only to survive but to imagine and sustain themselves and one another. The central question guiding this work is: How do Cubans harness disparate technological infrastructures to circulate censored or unofficial expressions of music and humor, and in doing so, reimagine what it means to be Cuban in a dispersed and mediated world?To explore this, I conducted a three-year ethnographic study that wove together digital fieldwork, in-person interviews, participant observation, and hermeneutic analysis. I follow four cultural forms that pulse through the digital archipelago: the music genres of Cubatón and Reparto and the digital humor practices of Instagram comedy and viral memes. I examine how these forms move across peer-to-peer file exchanges, Bluetooth transfers, social media timelines, and radio captures—offering insights into how identity and cultural life persist, evolve, and circulate, despite and because of constraints. I argue that Cuban cultural producers work within an archipelagic logic—one shaped by rupture, repetition, and relationality. Rather than follow linear or institutional pathways of circulation, the digital archipelago operates through rhythmic, improvised, and often fugitive infrastructures. Here, mobile phones, taxis, living rooms, hard drives, and bodies in motion become nodes of a scattered network defined as much by disconnection as by connection. These media ecologies echo Caribbean tidalectics and Creole sensibilities, revealing how Cubans articulate their sense of belonging and make meaning amid shifting material and political conditions. Ultimately, I propose the Cuban digital archipelago as both a cultural formation and a critical method: a way of theorizing digital culture, media infrastructures, and diasporic identity from the Caribbean and the Global South. By centering users' creativity and improvisational labor, this dissertation reframes the Cuban digital experience not as a story of disconnection or delay, but as one of endurance, alterity, and collective world-making.