This study has identified probable factors that govern ISMR predictability. Furthermore, extensive analysis has been performed to evaluate factors leading to the predictability aspect of Indian Summer Monsoon Rainfall (ISMR) using uncoupled and coupled version of National Centers for Environmental Prediction Coupled Forecast System (CFS). It has been found that the coupled version (CFS) has outperformed the uncoupled version [Global Forecast System (GFS)] of the model in terms of prediction of rainfall over Indian land points. Even the spatial distribution of rainfall is much better represented in the CFS as compared to that of GFS. Even though these model skills are inadequate for the reliable forecasting of monsoon, it imparts the capacious knowledge about the model fidelity. The mean monsoon features and its evolution in terms of rainfall and large-scale circulation along with the zonal and meridional shear of winds, which govern the strength of the monsoon, are relatively closer to the observation in the CFS as compared to the GFS. Furthermore, sea surface temperature-rainfall relation is fairly realistic and intense in the coupled version of the model (CFS). It is found that the CFS is able to capture El Nio Southern Oscillation ISMR (ENSO-ISMR) teleconnections much strongly as compared to GFS; however, in the case of Indian Ocean Dipole ISMR teleconnections, GFS has the larger say. Coupled models have to be fine-tuned for the prediction of the transition of El Nio as well as the strength of the mature phase has to be improved. Thus, to sum up, CFS tends to have better predictive skill on account of following three factors: (a) better ability to replicate mean features, (b) comparatively better representation of air-sea interactions, and (c) much better portrayal of ENSO-ISMR teleconnections. This study clearly brings out that coupled model is the only way forward for improving the ISMR prediction skill. However, coupled model's spurious representation of SST variability and mean model bias are detrimental in seasonal prediction.