Interactions between midlatitude disturbances and the monsoonal circulation are significant for the Indian summer monsoon (ISM) rainfall. This paper presents examples of monsoon–midlatitude linkage through anticyclonic Rossby wave breaking (RWB) over West Asia during June, July and August of the years 1998–2010. RWB events over West Asia are identified by the inversion of the potential vorticity air mass at three different isentropic levels (340, 350, and 360 K) using daily NCEP–NCAR reanalysis. It is observed that RWB took place over West Asia before/during breaks in the ISM. Further, these events occur on the anticyclonic shear side of the subtropical jet, where the gradient of the zonal wind is found to be high. RWB is responsible for the southward movement of high potential vorticity air from the westerly jet, leading to the formation of a blocking high over the Arabian region. In turn, this blocking high advects and causes the descent of upper tropospheric cold and dry air towards Central India. Such an air mass with low moist static energy inhibits deep monsoonal convection and thereby leads to a dry spell. In fact, we find that RWB induced blocking over West Asia to be one of the major causes of dry spell/break episodes in ISM. Additionally, the presence of cold air over Central India reduces the north–south thermal contrast over the monsoon region thereby modifying the local Hadley circulation over the region.