The city-state of Singapore's roadmap for internationalization of local companies into the GCC region has, arguably, made its mark; recently crossing the milestone of 100 local companies that have, to date, found business opportunities in this foreign and exotic land. Actually taking these opportunities, however, has proven more complicated, with cultural differences and highly dynamic local business environments posing unforeseen challenges to Singapore companies – producing a test of adaptability that has returned rather mixed results. Of particular interest are government-linked companies (GLCs), among the largest and the first of Singapore's entrants into the region; perceived as more structurally rigid, and with stakeholder obligations and motivations very much beyond the profit-driven. Thus, this paper – in which we explore the experiences of GLCs in the GCC, and draw some perhaps surprising conclusions.