This study investigates the role of convection–circulation coupling on the simulated eastward propagation of the Madden–Julian Oscillation (MJO) over the Maritime Continent (MC). Experiments are conducted with the European Centre Hamburg Model Version 5 (ECHAM5) coupled with the one-column ocean model—Snow-Ice-Thermocline (SIT) and two different cumulus schemes, Nordeng-Tiedtke (E5SIT-Nord) and Tiedtke (E5SIT-Tied). During the early phase of MJO composites, the E5SIT-Nord simulation reveals stronger intraseasonal anomalies in the apparent heat source (Q1) over the convective center, however, the E5SIT-Tied produces a stronger background Q1, suggesting that deep convection prevails over the MC but does not couple with the MJO circulation. Similarly, in the E5SIT-Tied simulation, in-column moisture is kept mostly by local deep convection over the MC, which is in contrast to the well-correlated relationship between moisture anomaly and MJO circulation in E5SIT-Nord. A case study based on an observational MJO reveals similar biases concerning of convection–circulation coupling emerges within a few days of simulations. The E5SIT-Tied simulation produces weaker heating at the convective center of the MJO than the E5SIT-Nord a few days after model initiation, resulting weaker subsidence to the east and less favorable for propagation. The present findings highlight the instantaneous responses of cumulus parameterization schemes to MJO-related environmental changes can further affect intraseasonal variability through altering convection–circulation coupling over the MC. Physical schemes of moist convection are essential to realistically represent this coupling and thereby improve the simulation of the eastward propagation of the MJO.