Confederate spy, Belle Boyd, began her career with a gunshot. In July 1861, Union troops arrived in Boyd's town and she wasn't too happy about it. Since her father was a member of the Confederate 2nd Virginia Infantry Regiment, Boyd (born Isabella Maria Boyd) was "supporting the troops" with Confederate flags in her bedroom.
The Union troops tried to confiscate the flags, then threw up the Stars and Stripes over her house. An argument ensued, a soldier cursed at her mother, and then Boyd pulled out a pistol and shot the guy. She was later cleared of wrongdoing — because in the 1860s it was totally cool to shoot people who cussed at women — but the Union began tracking her activities.
And interestingly enough, this Confederate spy used this to her advantage, and tracked them instead.
Union officials began to monitor Boyd's movements, but she used conversations with her minders to accumulate detailed information on their movements, sending the intelligence in letters to Confederate commanders. After one such letter was intercepted, Boyd escaped punishment by feigning ignorance. Her parents then sent her to live with her aunt and uncle in even tinier Front Royal (pop. 417), forty miles to the south.
In October 1861, after visiting her father's camp, Boyd began work as a courier between generals Jackson and P. G. T. Beauregard and was detained briefly for her efforts. Her oft-noted charm was a weapon and, occasionally, a liability. After being captured by a pair of Union soldiers, Boyd claimed to have sweet talked them into escorting her back to Confederate lines, where she promptly had them arrested. When Boyd's identity was revealed to the two hapless soldiers, they recognized it, suggesting that she already had attained something that spies tend to avoid—notoriety.
Notoriety is exactly what she found, as Boyd appears at least a few times in correspondence between senior Union leaders. While she was getting plenty of hate mail from the Union, she was earning respect from senior Confederates, to include General Stonewall Jackson, who made her a captain and honorary aide-de-camp, according to AP.
Perhaps her biggest intelligence "get" came in May 1862, as she spied on a Union general and his staff through a peephole in a closet floor (Great job securing the SCIF, guys). Union forces had recently captured Front Royal, Virginia, but the general was about to pull a large portion of his forces east. It wasn't long before the town was back in Confederate hands, thanks to Boyd's messages.