Purpose – Scotland’s built heritage is an important contributor to the economy and society as a whole. The purpose of this paper is thus to examine the challenges associated with the repair and maintenance (R&M.) of historic buildings with a view of informing practice. Design/methodology/approach – Two case studies of ‘live’ R&M. projects are reported of traditional (Project A) and modern stonemasonry practice (MSP) (Project B) to gain an insight of key site observations. Semi-structured interviews aimed to reveal project challenges and also an opportunity to discuss with stakeholders the wider issues facing the R&M. of historic buildings. Findings – Neglect and poor practice were found as key challenges for the successful R&M. resulting in time and cost overruns. These challenges were mainly attributed to poor skills development. Whilst the basic skills set for undertaking stonemasonry work, such as stone building, are fundamentally the same, they should be adapted to a particular project context. Both Project A and B utilised traditional stonemasonry with the use of modern materials and methods when specifying repairs to structural elements. Originality/value – This paper has provided original and valuable data using ‘live case studies’ (as opposed to post hoc data gathering) to highlight the importance of investment in skills development for conserving the existing stock of historic buildings. Indeed, it provides evidence of a continuing need to gain further similar direct data which will inform current skills development strategies as each R&M. project can present unique challenges.