This letter from George Washington (1732–1799) to his spymaster Benjamin Tallmadge (February 25, 1754–March 7, 1835) offers a behind-the-scenes look at how the commander-in-chief personally directed his intelligence operations. Writing in 1779, Washington gives instructions about communication routes for his agent “C.” (the alias of Abraham Woodhull (1750–1826), also known as Samuel Culper), weighing the safety and speed of different couriers and emphasizing the difficulty of supplying hard currency to fund the work. The document is accompanied by transcriptions of Culper’s own detailed intelligence reports describing British troop movements, ship arrivals, and embarkations in New York harbor. The Culper reports demonstrate exactly what kind of information the ring produced: granular observations about regiments, ships, and provisions that could shape Washington’s strategic decisions. This document showcases how intelligence flowed from an occupied city to the commander-in-chief, and illustrates the risks that ordinary informants took, since discovery meant almost certain execution.