The vast majority of research concerning street youth has focused upon etiology and street culture. Such investigations have been concerned with how young people enter street life and the myriad of activities associated with street survival. This paper takes a different, yet complimentary, approach and highlights the experiences of 20 Halifax street youth vis-à-vis information-communication technologies (ICTs). This study begins to explore how young people living on the street in one Canadian city understand, experience and access ICTs. Equally important, the study demonstrates the complexity, nuances and tensions of how and why street youth can feel both “hooked up” and “left behind” within an ever-emerging technology-driven global culture.