Entering the spy ring

Ann Bates was first discovered by a civilian-spy, John Craig, or "Craiggie". The two met sometime during British occupation in Philadelphia. Craig was an active member in Clinton's espionage network, and assigned Bates with small secret tasks while they were still in Philadelphia. Craig quickly noticed her intelligence, and referred her to meet with his general, Major Duncan Drummond, in New York City. She would then go on to flee Philadelphia on June 18, 1778, when British commander General Clinton evacuated his forces from the capital. General Clinton added Major John Andre as an aide and commander of his intelligence coordination, this is where Ann Bates became a member of Major Andre's spy ring.^[7] This was in response to news of an alliance between France and the United States. As the political climate was changing, Bates was one of many loyalists who left Philadelphia with the British Army. She swiftly left the capital after convincing the General at the time, Benedict Arnold, that she was leaving to sell her goods in New York City. After her husband joined Clinton's army on June 18, 1778, Bates followed the British to their headquarters in New York City. After she arrived at headquarters to meet with Craig, she was surprised to meet with one of Clinton's main spy handlers, Duncan Drummond, instead. The two persuaded Bates to join the British spy network. He was recorded describing their meeting; "A woman whom Craig has trusted often came to town last night. She is well acquainted with many of the R.A. (Royal Army)... It is proposed to send her out under the idea of selling little matters".^[3]

Washington's camp and the Rhode Island Campaign

On June 29, 1778, Bates left New York City for her first mission after only one day of training.^[3] She subsequently traveled to Washington's camp in White Plains, New York under the name "Mrs. Barnes". Because she was familiar with the artillery used during the Revolution, she was able to relay valuable information about the Americans' materials and strategy.^[2] Initially, Bates' mission was to find a disloyal soldier in Washington's camp who could give the British intelligence some potential intel, but she was unsuccessful in that mission. She then changed her mission while at the camp, and listened in on many conversations and counted artillery pieces on the camp.^[3] At George Washington's camp in White Plains, American troops were planning the Rhode Island Campaign. She recorded valuable intelligence on American movement into Rhode Island.^[2]

On her way back to New York City after her first mission, she was stopped at an American patrol stop four miles from White Plains for unknown reasons, and arrested at the check-point due to suspicion. Bates remained in confinement overnight, but was released the next morning. Once she finally returned to New York City, she relayed the vast information that she was able to gather to Major Drummond. She reported that American weapons were far more scarce than the British had originally believed them to be.^[2] General Drummond was impressed with her work, her memory, and her capabilities. Although Bates had just undergone a stressful mission, she was eager to return to White Plains again.^[2] She totaled three trips to the camp, and relayed information necessary for the British troops to combat American military efforts in the Battle of Rhode Island.^[2] In her third mission, she noted that 600 boats were being prepared to attack Long Island. Bates was able to give specific and important intelligence about the number of troops that were heading to attack British forces stationed in Long Island.^[3]

In September 1778, when she was on another mission infiltrating Washington’s army, a deserter from the British Twenty-Seventh Regiment recognized her, but she was able to elude capture.^[8] She then went on to travel through a series of safe houses that were designed for women spies at the time. She later wrote, "I had the Opportunity of going through their whole Army Remarking at the same time the strength & Situation of each Brigade, & the Number of Cannon with their Situation and Weight of Ball each Cannon was Charged with".^[3]

New Jersey and capture

During her final mission in White Plains, Ann Bates came across a former British soldier, a defector, who she suspected would report her after seeing her. She had recognized him from an earlier mission, and immediately left the American camp. She fled directly back to New York, and while doing so, cut straight through New Jersey. While traveling throughout that state, Bates stayed in Tory safe houses throughout the state. She wrote of the safe houses, "where I might be accommodated through the Jerseys."^[2] The expansive network of Loyalist safe houses throughout mid Atlantic proved to be effective. Many British prisoners were able to escape American camps from Virginia, up the east coast due to the effectiveness of the safe houses.^[2]

Bates wanted to get back to British lines as quickly as possible, for fear that her cover would be blown. On Saturday, September 26, 1778, on her way back to New York City, she was discovered at an American headquarters. The American unit had over 5,000 troops, and was under the command of General Charles Scott. General Scott was Washington's Chief of Intelligence, and was on the lookout for British counter-intelligence.^[2] Bates was detained and taken to Scott who questioned her. Bates told Scott that she "was a Soldier's wife in the Centre Division & had forgot something about five or six Miles below the Plains."^[2] Bates eventually was let go, but she was rattled by the occurrences, and suspicion that she was beginning to garner. After she returned to New York City and delivered information to Major Drummond, Drummond took her to Long Island with him for fear of her running into American forces again. A few days later they returned to Manhattan and Drummond asked her to meet with a friend of Benedict Arnold's within a 47-mile radius of Philadelphia. This displays Benedict Arnold's early involvement with the Tory intelligence network.^[2]

British advancement to Charleston

Between October 1778 and August 1779, Bates did not have any participation in Clinton's spy espionage network.^[3] This was due to Clinton sending Drummond back to England due to a disagreement between the two. Major John André went on to take Drummond's place.^[2] André was most well known for his collaboration with well-known American traitor, Benedict Arnold.^[9] In April 1780, her husband, Joseph Bates,^[2] was sent to Charleston, South Carolina to siege the city. Bates traveled with him there, but refrained from taking part in any further spy networking while in Charleston.^[2] An old friend, British Colonel Nisbet Balfour called for Bates' assistance in operating a spy ring out of Charleston. While there were plans for her to aid in General Cornwallis' mission to siege Charleston, both missions were aborted.