Establishing the Culper Spy Ring marked a change in American Intelligence's methods of gathering information. Previously, they had relied on a system of sending a lone agent into enemy territory who did not know the area or have any support system. Now they were using local residents with a series of connecting helpers, so that if one member was captured there would still be something left of the effort. Abraham Woodhull began spying using this new system on November 23, 1778, writing as Samuel Culper.
Woodhull's mission had a few serious flaws from the start. Woodhull was supposed to travel to New York City frequently, ostensibly to visit his sister, and wander the city gathering information. Besides the obvious problem that his visits had no real reason given the danger of traveling through the lines, Woodhull's visits were suspicious since he was from a family with Patriot ties and he spent his time in Manhattan wandering the city without good reason.
In June of 1778, Woodhull decided it was unsafe for him to continue making frequent trips to Manhattan and recruited his friend Robert Townsend to continue the Manhattan end of the business. Townsend had a good reason to be in Manhattan, and was readily able to provide Washington with good naval intelligence because of his job as a mercantile clerk. Townsend and Woodhull distinguished their dispatches by adding the phrase "Senior" and "Junior" to their dispatches. Townsend began sending reports on June 20, 1779.
Townsend's reports were good, but Washington desperately needed better Army intelligence. Townsend repetitively wrote that he could not get that information.
In the wake of these constant reports, Woodhull wrote of plans to recruit a new female helper and Townsend began taking out large sums of cash from his business. Within two months, Townsend was reporting top-level Army intelligence. By November, Townsend provided the Americans with information about a secret British operation to counterfeit American currency.
Townsend's November 27, 1779 report about British counterfeiting operations.