When he relocated to Shawneetown, he continued to read law with Judge William G. Bowman who had a large library of both law and the classics. In addition to his job as a clerk, he and his brother began their law practice using the name "E.C. and R.G. Ingersoll". During this time they also had an office in Raleigh, Illinois, then the county seat of neighboring Saline County. As attorneys following the court circuit he often practiced alongside Cunningham's soon-to-be son-in-law, John A. Logan, the state's attorney and political ally to Hall.