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A Work Project, presented as part of the requirements for the Award of a Masters Degree in Management from the NOVA – School of Business and Economics This work project had as a starting point a study developed by the consulting firm Roland Berger on how to boost the economic relations between Portugal and Germany. This paper aims to focus on a specific sector: Machinery and Equipment for a special purpose, and identify and describe concrete ways on how to increase the Portuguese export quota to Germany. The analysis results evidence that firms face different internationalization barriers depending upon their international focus. Nonetheless common barriers rely on a high emphasis on production to the detriment of sales and a lack of a cooperative mind-set among firms. A brief literature review is presented in regards to the former topic. Recommendations are suggested at three levels: governmental, sectorial and company level. At the individual company level, firms were organized in homogeneous groups depending on: (a) the willingness to export to Germany; (b) the stability of the business in the internal market, which is a proxy to assess the readiness to approach new markets in terms of production and financial health; (c) the active or passive attitude towards internationalizing.