This paper posits that the South China Sea (SCS) maritime dispute between an increasingly coercive China and the four Association of Southeast Asian Nations (ASEAN) claimants has reached a tipping point. First, ASEAN appears as unified as ever with its core states of Indonesia, Thailand, and Singapore wedded with its most vocal SCS claimants of Vietnam and the Philippines in pressing for a quick conclusion to the problem. Second, China has demonstrated an increased willingness to engage with ASEAN on the topic, departing from its usual demands for bilateral talks, in order to better relations with the bloc. Finally, a reasoned U.S. policy is providing resilience to ASEAN through a whole-of-government effort. These conditions offer tremendous opportunity for U.S. military support to efforts designed to strengthen ASEAN’s position vis-à-vis China. These military approaches include: active support to the establishment of a effective ASEAN Political Security Community; creation of opportunities for ASEAN to proselytize their views on a peaceful, multilateral solution; and, direct engagement with China and its military in order to influence its views on what constitutes an acceptable solution addressing its interests.