Conducting primary data collection can be a fulfilling and interesting adventure producing significant learning experiences particularly for early career researchers. However, fieldwork can be marred with complex challenges and frustrations, especially if conducted in dynamic and politically sensitive environments and with highly vulnerable urban populations. This paper contributes to and advances academic scholarship on fieldwork experiences in the social sciences. Drawing from the first author’s doctoral fieldwork experiences, we share our reflections on the application of the photovoice method in researching street traders in Harare, Zimbabwe. We engage with different issues that researchers could consider in the application of photovoice, especially with dynamic and marginalized urban populations like street traders. These include dealing with and managing complex and multiple ethical dilemmas, dealing with the content-quality conundrum, exploring ‘missing’ photographs and handling ‘leftover’ photographs, handling conflictual council-street trader relations, building rapport, and ensuring participant commitment, joint interpretation, and co-construction of meaning and methodological benefits of using photovoice with street traders. To the best of our knowledge, this is the first paper that reflects on the use of photovoice with street traders in Global South cities, and we hope that the insights presented here will be useful for future urban researchers working on similar topics.