Because of poverty following her father's death, Annie did not regularly attend school as a child, although she did attend later in childhood and in adulthood. On March 15, 1870, at age nine, she was admitted to the Darke County Infirmary along with her sister Sarah Ellen. According to her autobiography, she was put in the care of the infirmary's superintendent, Samuel Crawford Edington, and his wife Nancy, who taught her to sew and decorate. Beginning in the spring of 1870, she was "bound out" to a local family to help care for their infant son, on the false promise of fifty cents per week () and an education. The couple had originally wanted someone who could pump water, cook, and who was bigger. She spent about two years in near slavery to them, enduring mental and physical abuse. One time, the wife put Annie out in the freezing cold without shoes, as a punishment because she had fallen asleep over some darning. Annie referred to them as "the wolves". Even in her autobiography, she never revealed the couple's real names.