Abstract The goal of this thesis is to explore the possibilities of ‘qualitative research methodologies’ for research in Information System development. The reason for choosing these methodologies is the fact that they have to deal with ‘wicked’, ‘ill structured’ and ‘messy’ characteristics of their subject. These characteristics are also typical for the IS development problems. The different aspects of an IS development methodology can be described with the model of Seligman, using different ‘ways of’ modelling, -working, - controlling, -thinking and -supporting. In general, IS development is about creating different models on different levels of abstraction (product), using other models to guide the design process (process). The general strategy applied here is; if a development problem is too complex, it is split up into smaller pieces to make it manageable. Qualitative research differs from quantitative research in several aspects. In general, qualitative research is subjective, holistic, interpretative and inductive in nature, whereas qualitative research is objective, reductionist, experimental and deductive. Qualitative research has different paradigms; a spectrum starting with a ‘mechanical machine’ paradigm and ending in the more interpretative paradigms. The inductive, interpretive and holistic nature of quantitative methodologies makes concrete modelling as is known in information system development very difficult or even impossible. Qualitative research is therefore not very useful to ‘study way of working’ and ‘way of modelling’ since these aspects can be studied using (meta) models, and thus a more positivist (quantitative) research is in place. Qualitative research is very useful however to study the ‘way of thinking’; for instance exploring how a philosophy of a methodology is applied in a certain situation; compared to the philosophy that is described in the textbooks. On a more concrete level; the different research methodologies which are classified as qualitative have been studied. “How can these be applied to study information systems?” Each methodology has its own advantages and drawbacks, but they share a similar basis in the used paradigm. Because of this similarity, it is primarily the research goal and the research context which determines which methodology is to be used.