Large planning projects inserted in old cities often cause physical loss of the historic environments they encounter. Public actors face the challenge of conserving these environments, while simultaneously considering planning needs for the future. Departing from an understanding of conservation as the dynamic management of change, the thesis explores “compensation” for historic environment loss in response to urban planning projects. To do so, it delves into law and policy, theory, and practice. The thesis finds that in law and policy, the provision for compensation is severely inadequate, with environments largely being understood from the natural sciences perspective. This often connotes re-creation and/or relocation of the affected environments. In theory, historic environment compensation is inadequately researched, misunderstood, and often contested. And in practice, there are hardly any precedents for it. Given this background, the thesis fleshes out an understanding of compensation using two cases of large infrastructure projects that affect officially designated historic environments. The primary case is the West Link train tunnel in Gothenburg, Sweden, and the secondary one, the Mumbai Metro, in Mumbai, India. Findings show the presence of compensation in the West Link and preservation in the Mumbai Metro. Compensation is an additive and change-oriented response. It can take the form of conveying stories through signage, design elements, displaying excavated remains, as well as by creating entirely new public spaces and programmes at the urban scale. This is in contrast to preservation in the Mumbai Metro, which focuses on preserving the physical and visual integrity of the affected historic environment. The responses in the cases also reveal authorised views to varying extents, in the selection of certain historic environment values by experts. Further, compensation and preservation are heavily mediated by their planning contexts. They emerge through negotiations, are dependent on various institutional and policy frameworks, regulations, multiple actors and their approaches and mandates, and several constraints associated with these. In this context, it is often a challenge to implement more change-oriented approaches to conservation. Nevertheless, compensation offers a dynamic alternative to managing change to historic environments in moments of major urban transformation.