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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. Plain Language Summary: The observed seasonal rainfall regime, which varies over time, challenges the assumption of stable seasonal patterns in reconstructions of paleorainfall, suggesting that a reappraisal of the understanding of past ecological‐social changes with respect to rainfall may be needed. In this study, we have used a high‐resolution rainfall record from the Thai–Malay Peninsula and a state‐of‐the‐art transient paleoclimate simulation to describe a novel summer to winter rainfall regime shift during the Holocene era in the tropics, which may apply to regime‐boundary regions worldwide and thus provide a new perspective on dramatic ecological and social changes recorded around regime boundary regions for both past and future studies. Key Points: A unique rainfall record in the Thai‐Malay and a transient simulation suggest a summer to winter rainfall regime shift during the HoloceneTransient paleoclimate simulation simulation reveals that this shift was caused by westward migration of the boundary between summer and winter rainfall regimesThis regime shift could occur in regions around the boundaries of rainfall regimes in the tropics and possibly worldwide [ABSTRACT FROM AUTHOR]