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This article contributes to current debates around EU policy on territorial cohesion and its place-based approaches. Based on substantial empirical research in seven member countries in an on-going EU Horizon 2020 project, the article develops a conjunctural approach based on Doreen Massey’s conceptualisation of place to provide insight into how local development functions in spatial and temporal dimensions. One of the main objectives of the case studies is to compare policy programmes and practices that seek to alleviate territorial inequality and generate economic growth and territorial cohesion. In such a comparison, the issue of conflating and rescaling administrative territorial units and boundaries demands particular attention. Administrative boundaries do not necessarily reflect the complexity and interconnections between policy actors, businesses, and local communities. Local specificities make it difficult to compare the local political room for manoeuvre due to different administrative principles, unequal degrees of devolution of competences or differences in constitutions, e.g., federal states versus unity states. In this article, we argue that, faced with an analysis of highly diverse cases, a conjunctural analytical approach can help to capture and unpack some of the places’ complexities and regional interconnections and be a useful supplement to more conventional comparisons of more similar places. Through two examples, the article discusses what the application of this conjunctural approach means in practice, how it helped shape our understanding of how differently and how it can be further developed to accommodate place-based approaches to researching territorial cohesion.