Anderson resettled in 1815 on Drummond Island on what was believed at the time to be the Canadian side of Lake Huron, in another fur-trading community. Following the war, where Anderson attained the rank of Captain in the British army, he was appointed as storekeeper and clerk for the Indian Department of Upper Canada (then a part of the British army), a position he would keep for 43 years. Anderson remarried in 1820 to a woman named Elizabeth "Betsy" Hamilton, a member of a well-connected fur trading family with French, English and Ojibwe ancestry. Following the birth of their first child, Anderson, at the urging of his new wife, wrote to Grey Cloud in 1821 or 1822, inviting their children to live with his family indefinitely and receive an English education.
