With recent rapid digital evolution and integration of technology into our lifeworld, the suitability of causal based methods to study IT-entangled everyday experiences is becoming dubious. As interpretive research methods emerge as viable alternatives, some has criticized its rigor based on its less critical stance and lack of tools to understand complex historical and environmental influences on individual experiences. Drawing upon phenomenology, we propose Interpretive Phenomenological Analyses (IPA) as potential interpretive method of inquiry to understand how and why we engage with information systems. IPA provides a tool to both critical explore and hermeneutically interpret phenomena of lifeworld experiences based on users’ interpretation of their own experiences. The approach also provides a means to mapping out participants’ object of concern and their experiential claims using hermeneutical and critical questioning, then coherently contextualize participants’ interpretation within their environmental and cultural settings. We illustrate the proposed method with empirical evidence of excerpt from a longitude study of IS usage research. Consideration is given to philosophical assumptions, different IPA approaches, and researchers’ fore-structure presumptions of their field of interest. The paper intends to contribute toward the discussion of interpretive research methods in the field of information systems.