The U.S aviation industry faced severe financial losses after the 9/11 incident. The financial loss that occurred between 2000 and 2009 in the U.S. alone was $54 billion dollars. One of the operational strategies adopted by air carriers to overcome this hurdle was to outsource aircraft maintenance. Initially, this was accomplished in both home and off-shore locations. Unionized labor relations in the US ultimately forced these organizations to outsource to non-unionized labor sources in foreign countries. However, due to the upsurge in accidents and incidents that resulting from maintenance failures, the concept of outsourcing maintenance became a subject of debate and regulatory scrutiny. With regard to this debate and resulting safety issues, this paper discusses the concept of outsourcing and the trend of aviation outsourcing at a global level. It reviewed related risk factors by examining the root causes of several aviation-maintenance-related aircraft accidents that occurred in the US and abroad and identified the regulatory actions taken by the FAA and other concerned authorities to address the problem. Utilizing the results of a Strength, Weakness, Opportunity, and Threat (SWOT) analysis, along with the additional research conducted in the study, several recommendations were made. The first was to utilize enhanced data collection and analysis platforms that optimize decision-making and reduce downtime related to unscheduled maintenance. Next, the FAA and ICAO should mandate that all maintenance organizations, including those that are outsourced, implement Safety Management System (SMS) programs. A key component, however, is the incorporation of a reporting system that addresses human error within the SMS program such as the REPAIRER system.