This article explores challenges that surround the implementation of conservation management strategies for living heritage in the context of two case study sites in India. Acknowledging that, in theory, ‘bottom-up’ strategies for expertise exist but are rarely constituted in practice, it presents two vivid but fragile examples where such possibilities might be observed. It first distinguishes the Indian Cultural Heritage context from many conventional conceptions of heritage, defined by its distance from the beholder. Vignettes illustrate how the complexity of simultaneous value systems and beliefs may confound precepts relating to the treatment of tangible heritage. A discussion of the role of the architect in drawing and model making in this context is promoted for the purpose of deeper documentation. It draws upon previous work, which has proposed the enhanced potential to record the ephemeral as well as the monumental using photogrammetry. Building on this, the role of 3D digital models has recently been suggested as a means to contribute to processes for mediating between contested conservation strategies. Challenges of heritage that is at risk of destruction from being overwhelmed by nature are separated from those associated with dereliction or, in this instance and most importantly, increased use. The two case studies, in north and south India – at Ajmer in Rajasthan and at Madurai in Tamil Nadu – are discussed in relation to other examples. These present the opportunity to consider in context how issues of the designation of value at a local or a global scale might relate to corresponding difficulties in terms of governance and control at local or global scales. It again emphasises the role and scope of deeper documentation for this purpose. In terms of safeguarding, it suggests that better means for deeper observation of existing practices of maintenance should specifically be incorporated in future work.