Bradford covers 1639 and 1640 jointly, which allows him to fully explain a development that spans both years: the settlement of a dispute regarding the Plymouth and Massachusetts colonies' boundaries. By 1639, the colonies have expanded to such an extent that each, according to the other, is encroaching on the other's territory. The situation is especially tense in the neighboring towns of Hingham, which belongs to Massachusetts, and Scituate, where the Pilgrims have promised land to some of their investors. Eventually, the colonies decide to appoint four commissioners—two from each colony—to independently settle the issue. Despite initial disagreements between the commissioners, the colonies do ultimately sign an agreement on where the boundary should lie.

While these negotiations are going on, the Pilgrims are also attempting to reach an agreement with the partners in England. Over the course of 1639 and 1640, the investors send further letters to the Pilgrims complaining of Sherley's failure to pay and asking Winslow to return to England to help settle Sherley's debts. Winslow and the Pilgrims are reluctant, however, because they suspect that any representative they send over will again be arrested, "and an action for such a sum laid upon them that they would be unable to procure bail […] and that then the partners there could force them to do whatever they wished" (199).