Variability of hydrographic conditions and primary and secondary productivity between cold and warm climatic regimes in the Bering Sea has been the subject of much study in recent years, while interannual variability within a single regime and across multiple trophic levels has been less well-documented. Measurements from an instrumented mooring on the southeastern shelf of the Bering Sea were analyzed for the spring-to-summer transitions within the cold regime years of 2009–2012 to investigate the interannual variability of hydrographic conditions, primary producer biomass, and acoustically-derived secondary producer and consumer abundance and community structure. Hydrographic conditions in 2012 were significantly different than in 2009, 2010, and 2011, driven largely by increased ice extent and thickness, later ice retreat, and earlier stratification of the water column. Primary producer biomass was more tightly coupled to hydrographic conditions in 2012 than in 2009 or 2011, and shallow and mid-column phytoplankton blooms tended to occur independent of one another. There was a high degree of variability in the relationships between different classes of secondary producers and hydrographic conditions, evidence of significant intra-consumer interactions, and trade-offs between different consumer size classes in each year. Phytoplankton blooms stimulated different populations of secondary producers in each year, and summer consumer populations appeared to determine dominant populations in the subsequent spring. Overall, primary producers and secondary producers were more tightly coupled to each other and to hydrographic conditions in the coldest year compared to the warmer years. The highly variable nature of the interactions between the atmospherically-driven hydrographic environment, primary and secondary producers, and within food webs underscores the need to revisit how climatic regimes within the Bering Sea are defined and predicted to function given changing climate scenarios.