At the beginning of 21st century there has been an exponential increase in the production of the UAV systems. Today more than 700 different types of UAVs are being used for reconnaissance, intelligence and recently for combat. Bulk of these efforts primarily focuses on national security and war-fighting purposes. Almost nothing has been done for transportation which can serve for purposes ranging from military to life-saving humanitarian purposes. It is predicted that a paradigm shift for unmanned transportation will take place and the whole transportation system including cargo handling will switch to unmanned systems in the near or far future. However, there are challenges on this quest and they cannot be overcome by technology alone. This study explores the prejudgment of unmanned aerial vehicle systems being unsafe and aims to address constraints and concerns on technology, flight safety, and legal responsibilities. The potential bumpy areas that need governments' action through the unmanned aerial transportation road will be presented by analyzing the general problems faced in manned and unmanned flight.