Both observations and 20th century coupled model simulations suggest that severe weak monsoon years (seasonal mean rainfall less than 15% of the normal) over South Asia are associated with a developing El Nino. During these years and within the summer season, monsoon breaks last for a prolonged period (> 7 days). Detailed diagnostics show that dry advection is the primary initiator for the dryness while cloud-radiative processes maintain it. In all future RCP projections, a robust signal in the time-mean is a basin-wide SST warming along the equatorial central-eastern Pacific (El Nino-like conditions). Question of interests include: in a warmer planet, what is the probability that the monsoon extremes would increase and intensify? Are there any changes in the dynamical and thermodynamical processes that shape these extremes? To address the above questions, a series of idealized numerical experiments were performed in an ensemble mode. Model solutions suggest that compared to present-day, intensity of severe weak monsoons increases, and frequency and intensity of prolonged break conditions also increase. Furthermore, an examination of temporal evolution of area-averaged daily rainfall over South Asia suggests persistence of dryness throughout the summer season. Our model solutions imply the dominant role of boundary forcing, enhancing predictability of severe weak monsoons. The actual processes that shape these extremes as well as limitations in the present research, and future directions will be discussed.