Many of us live and exist in what David Killcullen refers to as urban littorals. These environments have been undergoing monumental change in terms of its infrastructure, social characteristics and the technologies we depend on as a city to live. The purpose of this talk is to provide an overview of wireless technologies that exist in a cities such as Singapore or even my home city of Sydney, and extend to Attendees and opportunity to go exploring to understand our dependencies and assess our resilience. I will analyse considerations of modern urban environments, pathways for wireless reconnaissance and mapping out the environment. My talk will seek to incorporate, tools techniques and methods for exploring wireless technologies through software defined radio, And finally some of the cool stuff I have observed over the years. Wireless technologies and our interdependencies are still very much the undiscovered country, and as such it is important that as professionals we seek to understand these environments as part of an integrated approach to better understanding risk.