This chapter critically examines the relevance of mainstream methods for assessing media freedom in countries where the state has limited authority. The case of the Somali territories illustrates the challenges of applying normative perspectives of how the media, and law, should be to how it operates in practice. Media across the Somali territories is both robust and pervasive, and intertwined with complex legal structures that are often regarded as "informal". The chapter considers several case studies of disputes involving ICTs and explores how they were resolved with legal tools available to the parties, which differs across the region. An alternative approach, termed a "diagnostic", is proposed to assess and understand media systems, while accounting for the informality that is often overlooked.