In the Sagar Island of Bay of Bengal, rainfed lowland rice is the major crop, grown solely depending on erratic distribution of southwest monsoon (SM) rainfall. Lack of information on SM rainfall variability and absence of crop scheduling accordingly results in frequent occurrence of intermittent water stress and occasional crop failure. In the present study, we analyzed long period (1982–2010) SM rainfall behavior (onset, withdrawal, rainfall and wetness indices, dry and wet spells), crop water requirement (CWR, by Food and Agriculture Organization (FAO) 56), and probability of weekly rainfall occurrence (by two-parameter gamma distribution) to assess the variability and impact on water availability, CWR, and rice productivity. Finally, crop planning was suggested to overcome monsoon uncertainties on water availability and rice productivity. Study revealed that the normal onset and withdrawal weeks for SM rainfall were 22nd ± 1 and 43rd ± 2 meteorological weeks (MW), respectively. However, effective monsoon rainfall started at 24th MW (rainfall 92.7 mm, p > 56.7 % for 50 mm rainfall) and was terminated by the end of 40th MW (rainfall 90.7 mm, p < 59.6 % for 50 mm rainfall). During crop growth periods (seed to seed, 21st to 45th MW), the island received an average weekly rainfall of 65.1 ± 25.9 mm, while the corresponding weekly CWR was 47.8 ± 5.4 mm. Despite net water surplus of 353.9 mm during crop growth periods, there was a deficit of 159.5 mm water during MW of 18–23 (seedling raising) and MW of 41–45 (flowering to maturity stages). Water stress was observed in early lag vegetative stage of crop growth (32nd MW). The total dry spell frequency during panicle initiation and heading stage was computed as 40 of which 6 dry spells were >7 days in duration and reflected a significant (p < 0.05) increasing trend (at 0.22 days year−1) over the years (1982–2010). The present study highlights the adaptive capacity of crop planning including abiotic stress-tolerant cultivars to monsoon rainfall variability for sustaining rainfed rice production vis-à-vis food and livelihood security in vulnerable islands of coastal ecosystem. © 2015, ISB.