Canada and ASEAN are political actors that avoid open conflicts and recourse to hard-power means. They pursue economic growth, regional military disarmament and peace. Despite these profoundly common strategic goals and diplomatic declarations on strengthening their bilateral cooperation, the relations between Canada and ASEAN seem to remain modest and circumspect, regardless of the fact that the cooperation has lasted since 1977 and that they established the enhanced partnership in 2009. Surprisingly, after nearly forty years of diplomatic interaction, the main cooperation pillar of this partnership has remained the socio-cultural and not the economic one, which was widely expected to fit the profile of the ASEAN–Canadian bilateralism. Despite advantageous preconditions, both actors eschew substantial economic exchange and high politics. This chapter presents the factors which account for such a constellation and explores the possibilities of deepening the partnership by emphasizing the so far largely missing strategic dimension of the ASEAN–Canadian partnership.