The development of rooftop solar PV generation has significant potential to generate enormous benefits to the electricity systems in achieving emission reduction targets and meeting increasing global energy demand, but could also make the power systems more resilient and affordable. In 2012, the Chilean government introduced a net billing law (Law 20.517) to incentivize consumers to sell their excess renewable electricity into the grid, which was expected to lead to a significant growth in rooftop solar. However, to date, the advancement of these technologies in the country has been very limited due to various barriers. For this reason, identifying and mitigating the main barriers that impede the advancement of development of rooftop solar is necessary to allow the successful deployment of these technologies. Based on data collected from a questionnaire survey and interviews conducted among the project developers in rooftop solar, the authors identify and rank the major barriers to the adoption of these technologies in Chile. Our findings show that the most significant barriers include “high investment and recovery period for the customer”, “lack of incentives to develop projects in the sector”, “rigid regulations regarding project size”, and “long administrative process and grid connection costs”. Furthermore, we discuss the most critical barriers in detail together with policy recommendations to overcome them.