New technologies provide potential increases in operational capability through improved survivability, mobility, and lethality. For technologies with a human in-the-loop, however, this potential is only translated to actual combat power through the expertise of the human controllers. This places training on the critical path for maximising the return on investment for technologies of this type. Modern systems also support distributed command and control through increased connectivity. To exploit this technology and seize the operational initiative, commanders must have the mental agility to respond as the situation changes and new information becomes available. This includes creating novel solutions when faced with unexpected situations. This places an emphasis on training to support greater personal adaptability. This paper discusses collaborative research by Rheinmetall Simulation Australia and the Australian Defence Science and Technology Organisation Land Division to investigate the impact of these issues on future training needs analysis and simulation-based training design in Defence. It discusses training as the selected sampling of the environment to provide the experience and feedback opportunities required for the accelerated development of expertise. Using this model, it evaluates the requirements for future Defence training, compares this with current approaches, and identifies a series of future research questions/“roadblocksâ€� for supporting the goal of more efficient, effective, and responsive simulation-based training. The discussion is intended to share Australian research with the international audience.