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This paper explores the colonialities of trans/gender and the Canary Islands to interrogate the in/adequacy of critical theory as a tool applied to Global South issues. In both cases, critical theory is found to be lacking due to its compulsion to predetermine and essentialise relations, which undermines its capacity to engage with the multiplicitous im/possibilities of trans/gender and post/coloniality. In lieu of a critical approach, the authors each engage with relational ontologies that offer a more capacious relationship with their respective colonialities. In the case of trans/gender, agential realism offers Pasley a means to trace the entanglements, potentiating more response-able becomings. For Ramirez, te Ao Māori allows her to imagine a future reconfigured to account for the multiple tensions that co-constitute Canary Island relationships with colonisation. While trans/gender and the Canary Islands are perhaps not an obvious pairing, the im/possibilities offered by each are deeply entangled in colonisation and the ongoing reconfiguration of colonialities in the pursuit of more just worlds. [ABSTRACT FROM AUTHOR]