Every year since Social Security began dishing out monthly benefit checks to eligible retired workers in 1940, the Social Security Board of Trustees has released a report outlining the financial state and outlook for America's top retirement program. Every Trustees Report since 1985 has estimated that Social Security wouldn't generate enough revenue in the 75 years following the release of a report to cover outlays, including cost-of-living adjustments. In plain English: Social Security is facing a long-term funding shortfall.