This paper assesses the extent to which strategic transportation plans and policies have succeeded at promoting elements of sustainable transportation in selected Canadian urban areas. The main hypothesis to be tested is whether the current prevalence of the “sustainability terminology” is merely an indication of the correct political jargon being adopted or a real sign that Canadian urban areas are becoming more sustainable. For this purpose, a review of existing official plans and transportation master plans in selected cities is initially conducted as a means of assisting in the development and implementation of a questionnaire-based survey. The survey is conducted with planners and policy makers at the three levels of government and it aims at capturing participants’ views on the existing mechanisms for appraisal, funding, and implementation of sustainable transport plans. The study confirms that while reviewed planning documents include sustainability objectives and propose strategies that can potentially improve the sustainability of transport, both funding and implementation have lagged behind. Interviewed participants have confirmed the disparity between political “wish lists” and actual funding for sustainable initiatives. This situation has led to a gloomy outlook towards the future of most Canadian urban areas on the part of most survey participants.