Historic 19th and 20th century buildings are currently facing the necessity of meeting contemporary needs such as adaptive re-use, energy efficiency, stability, and durability. The characteristics of architecture of these periods (i.e., material, design, details, maintenance, and functionality) increasingly make it challenging to maintain authenticity while incorporating new uses. Various strategies of technical interventions can be employed to achieve good results. This presentation will cover the case study of abandoned historic hospital pavilions from the early 20th century which are being converted into a high-end residential complex. The buildings face multiple challenges related to adaptive re-use, as they will be restored and connected with new infills and a glass connector and capped with re-creation of the historic cornices. The presentation will outline challenges of adaptive reuse through various technologies, leading to introduction of new elements and retention and upgrade of existing elements to incorporate new use.