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Since the 1990s, urban cultural policy in the UK has been bound to the cause of urban regeneration. Much has been written in examination and critique of this relationship, but what happens when the direction of strategic attention is reversed and civic leadership seeks to regenerate culture itself? The city of Glasgow, having made capital of culture over many decades, has moved towards a strategy for the development of literary Glasgow. This thesis documents a search for those factors crucial to that strategy. The research focuses on literary Glasgow as one aspect of the city’s cultural sector; identifies and examines gaps in the relationship between the civic cultural organisation and literary communities; and highlights those elements vital to the formation of a strategy for development of the literary in Glasgow. An extended period of participatory ethnographic research within the Aye Write! book festival and Sunny Govan Community Radio, is supplemented with data from interviews conducted across the literary sector and analysis of organisational documentation. Through these a gap has been identified between the policies and operations of a civic cultural organisation, and the desires of those engaged within the literary community. This gap is caused, in part, by the lack of a mechanism with which to reconcile contrasting narratives about the cultural essence of the city, or to negotiate the variations in definitions of value in relation to cultural engagement. The interdisciplinary approach builds upon insights from existing work within publishing studies, cultural policy, complexity theory and organisational studies to construct an understanding of the dynamics of Glasgow’s literary sector. This reveals the need for a framework in support of a landscape of practice, a desire for the placement of boundary objects to facilitate engagement, and the significance of value in relation to participation in literary activity. This work informs a strategy for literary Glasgow and contributes to conversations on strategies for cultural development in other cities.