Although characterized by generational shifts in terms of articulating cultural affiliations and attachments to both the Caribbean and Britain, Caribbean British writing remains deeply marked by issues of un/belonging. This essay explores this embedded thematic across changing political contexts and reads the transitions in Caribbean British literature that have brought different revisionary perspectives on literary forms and languages, post-Windrush British history and the much deeper historical connections between the Caribbean presence and the UK. As well as contesting racism, these works articulate intersectional identities informed by class, gender and sexuality as it is experienced within and across the UK and the Caribbean. Given that contemporary Caribbean British literature is very much connected with Caribbean literature and that of the larger diaspora, this essay considers the modes of critical attention necessary to engage with its new forms and platforms.