The seasonal rainfall regime is a key factor control on local ecological and social processes and is commonly thought to be stable under long‐term climate changes. Here we present a unique high‐resolution rainfall record from the Thai‐Malay Peninsula, combined with a state‐of‐the‐art transient climate simulation, demonstrating a fundamental rainfall regime shift from summer to winter during the Holocene. Transient model simulation and new sensitivity experiments further reveal that westward migration of the boundary between summer and winter rainfall regimes results in a summer to winter rainfall regime shift forced by distinct changes in summer and winter monsoons. Our findings suggest that the seasonal rainfall regime could be unstable under climate change around the boundaries of rainfall regimes in the tropics and possibly worldwide, which might be more critical for shaping both past and future ecological environments.