Somaliland’s Private Sector at a Crossroads is the World Bank Group’s first effort to undertake a consultative in-depth analysis of the private and financial sector in Somaliland in at least a generation. The objective of the report is to take stock of what has been achieved since the 1999 constitution was approved, provide an assessment of the current evolution of the private sector, and identify some priority policy options and related actions that would best enable the private sector to generate the growth and jobs sought under the Somaliland National Development Plan. The report is structured around the three key sector actors of the economy: enterprises, financial institutions, and the government. This approach has been taken to facilitate a political economy lens into the analysis. The report explores trends in, opportunities for, and impediments to effective government regulation of the private and financial sector and private sector-led economic growth in Somaliland, a relatively new democracy with limited institutional capacities. Drawing heavily on feedback received through an extensive consultative process that was undertaken in tandem with the analysis, the study concludes with recommendations for policy choices for the continued robust growth of the private sector and the evolution of a sounder financial sector.