Timber is found in many structures around the world and has been an important building material for centuries. As buildings and structures continue to age and are adapted for changing needs, steps to conserve associated heritage values and the physical aspects need to be taken. An investigation into current methodologies and resources to aid in the conservation of historic heavy timber structures was conducted. A proposed methodology is applied to case study of the roof structure of the Governor General’s Pavilion on East Block. Site visits, truss frame analysis and traditional timber connections assessment identify challenges of code applicability and the need for better resources. Parametric analysis comparing support conditions and material grade demonstrate behavior and capacity changes in the structure. Retrofit strategies are discussed.