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Over the last 10 years, small- and medium-sized enterprises (SMEs) in developed countries have faced increasingly stiff competition in their local markets, which has put the survival of many of them at risk. To reduce their vulnerability, many SMEs have targeted sales to other countries. Recently, however, the pace and intensity of these firms’ export activities appear to have decreased, as their traditional markets (i.e., the United States and Europe) have been experiencing slow growth. This situation has led some SMEs to explore the possibility of exporting to less traditional countries presenting more opportunities. However, a good number of entrepreneurs remain hesitant to go down this road, in particular given the uncertainty that prevails in those regions and the risks they represent in terms of exports. This study, which was conducted with a sample of 582 Canadian manufacturing SMEs, reveals that two characteristics help explain the fact that some SMEs choose to export to higher risk countries, more specifically to Asia. These characteristics are a positive attitude towards risk-taking among managers and the implementation of certain risk management mechanisms.