Amanda first met Robert Faulkner when she was a teenager. They sent letters to each other until Robert stopped when he went to join the Assassins, but even though Faulkner had disappeared off the grid completely, Amanda still had hope that he was still alive, and set off to look for him. Her search was fruitless, though, and she eventually acquired a job at Martha's Vineyard; she would later go on to purchase the establishment.
During the American Revolution, Amanda was a spy for the Continental Army. Her independent spirit was also responsible for setting up the first school in the area, and she also improved the docks near Martha's Vineyard to bring in more business for her inn. However, knowledge of her role as a spy has only been known since 1919, when a box of Amanda's personal correspondence was found, including coded notes in Benjamin Tallmadge's handwriting.
In 1773, Amanda met Robert Faulkner again, who had traveled to Martha's Vineyard with Connor, hoping to recruit David and Richard Clutterbuck and buy cannons for the Aquila. While there, Connor nearly started a fight with Benjamin Church and Nicholas Biddle, but Amanda managed to diffuse the situation before it really started.
Amanda met with Faulkner once more in 1776, this time on the Aquila, which had been waiting for her near Nantucket. There she told Connor and Faulkner the rumors of Biddle raiding ships along the East Coast. The Aquila was then forced to rescue a merchant ship from Templar vessels, during which Amanda hid out on the gun deck, from where she could witness the events.