Abstract: Seen through the eyes of a determined terrorist the city is full of opportunities. Car bombs, hidden explosives, toxic gases, handheld weapons; they can all be used to devastating effect on a crowded city street. While intelligence gathering, surveillance and police presence are key counter terrorism tools the last line of protecting potential targets are typically barriers and security checks. These additions to the cityscape can be an inconvenience, add little to local aesthetics and constantly remind us of the ever-present danger of terrorism. The Designing Out Crime Research Centre undertake projects which aim to protect Sydney from such attacks in ways which are sympathetic to the local environment and to the untrained eye have little connection to protection against terrorism. This paper outlines the threats to the city and countermeasures illustrated by case studies including projects for Sydney Rail, and the Sydney Opera House.