There were still some unresolved questions about boundary designations in most of the early deeds, which often led to endless bickering and lengthy court challenges between the settlers. The Andros and Dongan Patents had not examined the Indian deeds with any degree of scrutiny. In both cases the colonial governor merely wanted to raise revenue and to establish the principle of Crown approval for any future land transactions with Indians. As long as no serious challenge to the Southampton land titles threatened, the proprietors felt quite safe.

This complacency was soon disrupted rather dramatically. Lord Cornbury, certainly one of New York's more colorful governors, gave two members of his Council a most unusual grant. Rip Van Dam and Dr. John Bridges were licensed to buy up all unappropriated Indian land on eastern Long Island in September of 1702. They moved rapidly to press local Indians groups to sell all of their lands which had not been included in earlier transactions. The two agents from New York appear to have used another of the strategies listed by Jennings. They were accused of using "trickery and strong waters" in their negotiation with the Montauk Indians.. Marion Fisher Ales, writing on the Montauk suggests that Van Dam's agents were also aided by a long-festering animosity between the Montauk and the townspeople of East Hampton. The result of all of these factors was a deed which gave the eastern tip of Montauk to Rip Van Dam. All of this had been accomplished in less than six weeks.

The towns of Southampton and East Hampton were virtually in a panic over Van Dam's activities. They needed to review their Indian deeds with an eye to any opening which could be used by Van Dam. The eastern boundary of the 1640 deed was still troubling to the Southampton proprietors. The only documentation they had for the land between the Shinnecock Hills and Wainscott would certainly not survive a court challenge. The proprietors decided to protect their land from Van Dam by negotiating a new deed with the Shinnecock.

In a week-long frenzy of negotiation the proprietors managed to get five important documents signed by the Shinnecock and one by the Unkechaug. It was quite an accomplishment; for the Indians it must have been a bewildering experience. Over a sixty-year period beginning in 1640, the Shinnecock had signed seven or eight major documents; now in one week's time they had been pressured to sign six. The town's concern for a document which carried the full weight of the community led them to identify the party of the first part as the Trustees of the Commonality of the Town of Southampton. The legal implications here are significant. The term 'commonality" included the proprietors and all the other free men of the colony who did not own a share in the unallotted lands. This strategy drew the town into a solid front against any effort by colonial authorities to challenge the agreement. The negotiations began, ironically, on Friday, the thirteenth day of August, 1703. The first round of negotiations appear to have included Abraham Howell, Stephen Boyar, Arthur Davis, John Davis, John Wheeler and Benjamin Marshall for the Town and for the Shinnecock, Pongamo (Mandush's son), Chice, and Manamam. The Unkechaug sachem, Wyongonheot (Wiangonhut), was also included in the negotiations because of his interest in the Quogue land titles.