This thesis examines relations between Wales and the German Democratic Republic (GDR) during the Cold War period of 1949 to 1990. Previous studies have investigated who in Britain interacted with the GDR and their motivations for doing so. The appeal of particular groups and demographics to the GDR authorities - in pursuit of foreign policy objectives - are also well documented. This study is driven by two research questions: i) the identity and motivations of Welsh individuals or organisations approaching and engaging with the GDR and considering to what extent their ‘Welsh identity’ influenced their positioning vis-à-vis the GDR and the Cold War; ii) the extent of Welsh acceptance of any overtures made by a socialist state, including the likely resonance of the GDR’s self-promotion as an anti-fascist, egalitarian state, which sought to protect and develop the rights of its own Sorbian minority culture. The research approach adopted for the thesis has considered how multiple projections of ‘Welshness’ influenced the expression of, and thus the GDR’s perception and understanding of Welsh identity. The findings from this research suggest that the most intriguing and recurrent interactions between Wales and the GDR occurred as a result of concerns for the status of the Welsh language during the Cold War period, encouraged by the GDR’s domestic policy for its own Sorbian minority. This study thus contributes a further category of Welsh-speakers to those identified in the existing scholarship as having interacted with the GDR. Notwithstanding Welsh-Sorbian interactions, this research also determines that other facets of Welsh life sought to engage with the GDR, including representatives of the friendship movement, the Welsh proletariat and left-leaning politicians who believed that establishing relations with the GDR would facilitate détente and peaceful co-existence. Existing assumptions in the field are further strengthened by this thesis’ findings, including the GDR’s methods and approaches for cultivating relationships with the West. Varying projections of Welsh identity prompted different (and often confused and inappropriate) responses from the GDR authorities. By evaluating a range of Welsh-GDR interactions throughout the Cold War period, the findings of this research contribute an alternative Welsh narrative to the field of British-GDR relations.