In this case study, I outline some of those research constraints and ethical dilemmas which may arise when attempting to access and interview hard-to-reach, and often high-risk, sample groups and how rapport building may ease this process. Although Scotland’s largest city, Glasgow, has a long and synonymous history with gangs, in the contemporary era, the label “gang” has come to be used to describe what are essentially recreational delinquent youth groups. Many scholars have pointed out that such groups are anything but gangs per se. Therefore, in seeking criminal gangs more akin to those being identified in the Anglo-Welsh and North American contexts, eventually 40 in-depth qualitative interviews were conducted with practitioners (n = 5) and (ex)offenders (n = 35) involved in what Police Scotland terms “Serious and Organised Crime”: primarily in the form of mid-level brokerage within illegal drug markets. This case study opens by chronologically outlining the research methods chosen while undertaking the study, to aid early career researchers’ insight into the research process, before reflecting upon some of the difficulties involved in, and ways around, accessing particular sample groups and exploring constraints and ethical issues which may arise.