In this paper I reflect on the community entry phases of doing critical ethnography in a traditional Zulu community in a deep rural part of South Africa. I present my reflections in the form of a confessional account on community entry and on how an ICT4D project was introduced in the community. The primary research question that guided my engagement in the project is: In what ways should I achieve self-emancipation, in order to ensure the on-going emancipation and empowerment of the people I engage with? I thus argue that the emancipation of the researcher is a precursor for the emancipation of the researched. The paper is practiceorientated in that it demonstrates how community entry was established in a particular situation, how community entry encounters informed followup work, and how cultural interpreters empowered me to do community entry successfully. Through confessional writing I reflect on the beginnings of criticality in fieldwork practices and how I recognised, exposed, and articulated my own inabilities, social entrapment, and need for emancipation in ICT4D work. The paper concludes with guidelines for ethical community entry conduct in situations similar to what I encountered and for doing critical research at the grass-roots level of practice.