Industrial heritage is a sensitive word in architecture and urban design, bringing the coexistence of both limitations and opportunities in practical projects. During the past 20 years or so, a gratifying trend of reconsidering industrial heritage’s value in the UK has gradually prevailed globally. Simultaneously, the rapid growth of modern cities urged the necessity of dealing with left-over industrial places appropriately. People can see an acceleration of interest in studying the social elements of industrial heritage quarters within the city because preserving such heritage needs the inclusive participation of any relevant people, community, organizations, and stakeholders. In such circumstances, contextually sensitive analysis was proposed based on both a preservational and developmental perspective to assist in planning and analysing industrial heritage regeneration projects. Contextually sensitive analysis (CSA) originated from the contextual thinking in the urban study and design. It aims to concretise the over-sloganized prospects of current sustainability and address the importance of social aspects by considering the sensitivity of context impacts into consideration, context-sensitive analysis is a mixed-method strategy to explore how the regeneration strategies of industrial heritage contribute to the ongoing success of social sustainability. It will provide a quantitative way of visualizing the regeneration impact and outcome towards a socially sustainable industrial heritage quarter. Taking the eight UK industrial heritage regeneration projects as samples, the results visualize impact trends of the regeneration schemes on the performance of social sustainability. The result of the influence will illustrate how socially sustainable regeneration can be achieved through heritage re-identification, industrial space revitalization, and collaborative planning and management.