The climatological Asian summer monsoon (ASM) is decomposed into the slow and fast annual cycles (SAC and FAC). The FAC represents the abrupt onset and breaks phase-locked to the ASM seasonal progression. This study evaluates how well the NCEP Climate Forecast System version 2 (CFSv2) simulates the SAC and FAC over the Indian and East Asia monsoon regions (IMR and EAMR). The simulated SACs are in good agreement with observations in both regions. The FAC also represents the northward propagation in both observations and CFSv2. It is further demonstrated that the FAC is associated with a thermodynamic air–sea interaction. In particular, the different roles played by the wind-evaporation-SST (WES) feedback may account for the faster propagation in the IMR than the EAMR. However, compared with observations, the simulated FAC shows earlier monsoon onset and long-lasting stronger dry and wet phases in the IMR but delayed monsoon onset with weaker and less organized FAC in the EAMR. These reversed behaviors may originate from a warm (cold) SST bias in the IMR (EAMR) in boreal spring and enhanced by an overly sensitive surface evaporation to wind changes in the CFSv2. As a result, the warm spring SST bias in the IMR initiates a strong WES feedback and changes of solar insolation during boreal summer, which leads to a cold SST bias in early fall. On the other hand, the cold spring SST bias in the EAMR accounts for a weaker air–sea coupling, which in turn results in a warm SST bias after the withdrawal of the monsoon.