Tailer eventually returned to Massachusetts. Under Shute's governorship he was several times involved in negotiations with Indians on the northern frontiers, and continued to be active in the provincial militia. Tailer accompanied Shute on an expedition to Maine to negotiate with the Abenaki of northern New England in 1717. Shute handled the negotiations poorly, raising tensions between the Abenaki and British settlers. In 1720 Tailer was one of several commissioners sent to mediate between the settlers and Abenaki. Although a potential basis for agreement was identified, continued raiding and disagreement on the details of proposed terms caused the situation to deteriorate further. Shute declared war on the Abenaki in July 1722 following raids against British settlements on the Maine coast.