Characteristics of the Indian and Australian summer monsoon systems, their seasonality and interactions are examined in a variety of observational datasets and in the Coupled Model Intercomparison Project Phase 3 and 5 (CMIP3 and CMIP5) climate models. In particular, it is examined whether preferred monsoon transitions between the two regions and from one year to another, that form parts of the Tropospheric Biennial Oscillation, can lead to improved predictive skill. An overall improvement in simulation of seasonality for both monsoons is seen in CMIP5 over CMIP3, with most CMIP5 models correctly simulating very low rainfall rates outside of the monsoon season. The predictability resulting from each transition is quantified using a Monte Carlo technique. The transition from strong/weak Indian monsoon to strong/weak Australian monsoon shows ∼15% enhanced predictability in the observations, in estimating whether the following monsoon will be stronger/weaker than the climatology. Most models also successfully simulate this transition. However, enhanced predictability for other transitions is less clear.