This article argues that the U.S.–Southeast Asia relations under Obama have been driven and limited by a “partially converged hedging” process between the two sides. On the one hand, the United States has sought to push back and hedge against the longer-term risks of a rising challenger by mobilizing its alignment and diplomatic assets in Asia. The structural imperative, however, has been conditioned by a calculation of not wanting to be rigidly locked in any regional problems. On the other hand, the ASEAN states have correspondingly hedged against the uncertainty surrounding China's rise by leveraging on the United States' enhanced engagement. This driver, nonetheless, has also been conditioned by a fundamental concern of not wanting to confront the rising power in an outright manner. Unless China's actions have posed an immediate threat that leaves the states no choice but balancing, such a partially converged hedging process is likely to endure in the years to come.