He had a close call at the end of this assignment and had to make his way through enemy lines after his escape. Following this he returned to scouting and picket duty. Stringfellow served with Stuart at Seven Pines and Cold Harbor. In July, 1862 he was put on independent scout duty by Stuart in order to reconnoiter Pope's army. In August, he located a large wagon train at Catlett's Station and led Stuart to it, almost capturing Pope in the process. Left behind at Cedar Run to watch enemy troop movements, Stringfellow was again almost captured by Yankee soldiers.

In the winter of 1863 Stringfellow returned to Alexandria to gather intelligence, having set up communication lines throughout Fairfax County. He was spotted in Alexandria, however, after he had been there only a short time. He managed to escape by hiding under the hoop skirt of a elderly Confederate sympathizer when pursued by Federal troops. Shortly after leaving Alexandria, angered by the killing of two of his men, he and a troop of about 35 Confederates attacked about fifty Yankees in house, killing and wounding many of them and taking about 25 prisoners.

In June, 1863 Stringfellow had another amazing escape. He was dining with some friends in their home near the Bull Run Mountains when they were surprised by Federal troops. Stringfellow was well known to the Yankees by now and a constant target of their search. This group had orders to kill him on sight. Aided by a black female servant, Stringfellow was able to find a tight spot in the attic to hide in. The Yankees searched high and low in the house and barely overlooked him. He then slipped out of the house, commandeered a horse from a Federal he surprised and made his escape. His luck ran out later that month, however, when he was captured and sent to Old Capitol Prison in Washington City. He was exchanged as a Captain in August. Later that month he led a raid with eleven other Confederates on a Federal Headquarters and almost succeeded in capturing another Yankee General.

In late September Stringfellow was on patrol with 2 comrades. While they were asleep 4 Yankees surprised them. Stringfellow was able to kill 1 Yankee and his comrade killed another. The other Confederate was shot but the remaining Yankees took off to alert their camp. The 2 Confederates separated, pursued hotly by the Yankees. Stringfellow escaped by hiding under a fallen cedar tree while the Yankees searched all around him. The 2 Confederates were then able to reunite and escape.

In late 1863 there was fighting around Stringfellow's boyhood home in Culpepper County. His mother was wounded in the foot and taken by the Federals in order to treat her injury. She was being held in a house that was in an area serving as a Federal regimental headquarters. Stringfellow got inside the Federal encampment and found his mother. He borrowed a woman's dress and bonnet from his mother’s female servant (who was still with his mother), slipped into the house and tended to his mother for 2 days before slipping out again and heading back to Confederate lines.

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