Now, as you know, getting back and forth with a gigantic bounty on your head isn't easy. She dealt with her narcolepsy and trying to stay away slave patrols (paddy rollers) and slave catchers. Another big problem in her life was her husband. While on a mission, Harriet stopped by to see him. She wore her best clothing and braided her hair. When she got there and the door was opened, she saw why he hadn't contacted her. He had remarried. She was heartbroken, but that incident didn't make her weak. It made her stronger. 
    On another mission, Harriet had to go through town to get food. She carried chicken to keep her hidden. While she was walking, she spotted her former master walking right towards her. She quickly dropped her chicken and ran to catch them so her old owner wouldn't recognize her. Harriet surely took a lot of risks, but she succeeded and was never caught. But one mission almost got her caught, and jailed for good.
    Harriet helped eight slaves from Dorchester County plan an escape. Her father sheltered the runaways in his home. Harriet had told them to contact a Thomas Otwell, a free black man and an Underground Railroad conductor, in Dover, Delaware. Unfortunately, Otwell betrayed the group for a $3,000 reward to catch them. Instead of guiding them to the north, he guided them to jail. Luckily the group escaped.
    An investigation took place to capture the group. They had many suspects and one was Ben Ross. They rightly suspected that Ben Ross's house had been used as a hideout for the group, now called the Dover Eight. Before they could arrest them, a Anthony C. Thompson warned Ben and told him he needed to leave. Harriet went back to Maryland to get her mother and father. Because they were older, Harriet had to buy a horse and make a carriage for them to ride in.