Although decolonial thought from Latin America and the Caribbean is a multifaceted field of research and sociopolitical praxis, it is often interpreted monolithically. To refuse this tendency, we argue that it is imperative to trace decolonial theory's intellectual genealogies and engage in transgressive decolonial hermeneutics to re-interpret texts (theories) according to their living socio-historical and geopolitical contexts. Following Stuart Hall's lead, we first sketch out the geopolitical and sociocultural exigencies that allow for theoretical movements to unfold, paying more attention to the geopolitical implications of thinking "from" Latin America and the Caribbean. Second, we address the ethical imperative of thinking "with" as we seriously engage in inter-epistemic dialogues to advance an ecology of decolonial knowledges and pedagogical practices born in struggle. Ultimately, this article situates decolonial discourses and practices according to the conditions that enable their praxis-oriented intellectual expression.