In the Bay of Bengal, the warm, dry boreal spring concludes with the onset of the summer monsoon and accompanying southwesterly winds, heavy rains, and variable air-sea fluxes. Here, we summarize the 2018 monsoon onset using observations collected through the multinational Monsoon Intraseasonal Oscillations in the Bay of Bengal (MISO-BoB) program between the US, India, and Sri Lanka. MISO-BoB aims to improve understanding of monsoon intraseasonal variability, and the 2018 field effort captured the coupled air-sea response during a transition from active-to-break conditions in the central BoB. The active phase of the ~20-day research cruise was characterized by warm sea surface temperature (SST > 30°C), cold atmospheric outflows with intermittent heavy rainfall, and increasing winds (from 2 to 15 m s−1). Accumulated rainfall exceeded 200 mm with 90% of precipitation occurring during the first week. The following break period was both dry and clear, with persistent 10−12 m s−1 wind and evaporation of 0.2 mm h−1. The evolving environmental state included a deepening ocean mixed layer (from ~20 to 50 m), cooling SST (by ~ 1°C), and warming/drying of the lower to mid-troposphere. Local atmospheric development was consistent with phasing of the large-scale intraseasonal oscillation. The upper ocean stores significant heat in the BoB, enough to maintain SST above 29°C despite cooling by surface fluxes and ocean mixing. Comparison with reanalysis indicates biases in air-sea fluxes, which may be related to overly cool prescribed SST. Resolution of such biases offers a path toward improved forecasting of transition periods in the monsoon.