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In the field of development, Information & Communication Technology (ICT) is often hailed and cursed at the same time. ICT offers great promise to enhance development activities' efficiency and effectiveness yet the literature is littered with examples of failure. A particular challenge concerns the application of ICT to support collaboration in development contexts. In this paper, we report on field experiences with one particular type of collaboration technology, Group Support Systems (GSS), and its role in supporting groups engaged in development activities. Being an North-American invention, research into GSS is predominantly focused on Western Euro-American settings. GSS field studies in other cultural environments are scarce. The objective of our study is to explore and compare the applicability of GSS in two particular environments: Tanzania and South Africa. Our data suggest that the use of GSS is evaluated positively in both countries, although Tanzanian groups perceived more benefits. In South Africa, top management displayed very open and non-conservative behavior towards the technology, while in Tanzania hesitance from top management can be expected to be the greatest hindrance for GSS acceptance and application. The data further indicate that GSS do not replace existing meeting customs, but rather introduce new ones that co-exist next to the traditional ones. A key difference between application of GSS in western and African environments is a stronger focus on the electronic part of discussions in Africa. Anonymity is perceived as the key feature. [ABSTRACT FROM AUTHOR]