What does it take for an open source, Not-for-Profit, software developed in one context to be internationalized and localized so as to be used in another context different from its origin. This question is addressed in the frame of a Health Information System application developed in and for South Africa and subsequently transferred to use in Mozambique. Through an action research effort, five sets of key challenges to cross-country translation process have been identified: (i) language rules and lack of Portuguese equivalent terms from English, (ii) length of strings, (iii) different naming conventions, (iv) different organizational structures, and (v) inadequate knowledge. The understanding of these challenges helps us to identify the different features of translation associated with “general purpose” and “special purpose” applications. The analysis helps to address the question of how a “pragmatic balance” can be obtained between the needs for creating internationalized products on one hand, and that for providing flexibility for local adaptation on the other hand.