Purpose: Doing qualitative research with vulnerable urban populations such as street traders present significant methodological challenges, which many researchers may not be prepared to handle. This paper aims to provide a reflective account of the authors' fieldwork experiences while conducting a study with street traders in Harare, Zimbabwe. Design/methodology/approach: This paper draws data from a qualitative case study conducted with street traders in Harare's Central Business District (CBD). In this study, mixed qualitative methods were used including focus group discussions, semi-structured interviews and photovoice. Findings: The study's findings suggest that researching street traders is a complex process that requires flexibility, adaptability and creativity of researchers across the following aspects: gaining access in unfamiliar research contexts, building rapport and trust with participants, managing ethical dilemmas and addressing power imbalances between researchers and participants. Originality/value: While there is a growing body of empirical research on street trading in the global south, there are limited studies that discusses the practical fieldwork experiences associated with conducting primary research with such vulnerable and dynamic urban populations. The authors highlight strategies and practical steps that can be taken to address these challenges. This paper emphasizes the need for flexibility and adaptability in researching street traders, as it is akin to exploring uncharted territories where conventional methodological templates may not be effective.