East Java, Indonesia is a region with many climate risks including El Niño-Southern Oscillation (ENSO) related droughts and high rainfall variability which threaten the agrarian livelihoods of its population.  For the Pacitan District of East Java, one predominated by subsistence farming, we evaluated ENSO forecasts ahead of critical crop planning periods, crop productivity and precipitation data from 1990-2008.  July-August-September’s (JAS) ENSO forecast provides an indicator of the character of rice productivity in the following year’s harvest.  December-November-January (DNJ) ENSO forecast provides an indicator of the character of soybean productivity in the second growing season's harvest.  October and December are identified as key monthly rainfall totals that impact rice productivity, January for maize productivity and February for soybean productivity.  The implication of this timing and information is that it allows for management strategies to be implemented accordingly.  Improving year to year climate risk management strategies in a timescale manageable for small holders can ultimately prove beneficial for improving productivity and adapting to a future variable climate.