The inevitable changes to the built environment over time presents the question of what contemporary design is appropriate for existing historical context. This is inherently a wicked problem that is becoming increasingly important to designers in the 21st century. Wicked problems, as the connotation implies, are those that are multi-faceted, unique, and with innumerable possible solutions (Rittel, Webber 1973). Each individual architectural project is a cog in a city’s evolving machine, therefore no one project should ever be considered unimportant. As Robert Venturi said in his “Gentle Manifesto”, a designer should strive towards “messy vitality over obvious unity” (Venturi, 1966). Finding a simple design resolution is difficult if not impossible in a complex urban city layered with centuries of architecture. It is not necessary to copy the historic building next door, nor is it appropriate to design as if a site has no neighbors. The surrounding context should be evaluated for its mass, scale, program, history, and materials, among others, to inform and inspire a contemporary designer’s work. This thesis offers no “solution”; rather a series of design considerations. These considerations are by no means prescriptive, however. My aspiration is that this thesis can be used by future designers as a tool to prompt discussion and discovery about their own site specific project. / Master of Architecture