A fire team breaches a two story building, quickly suffering casualties; an infantry platoon comes under mortar fire while conducting a cordon and search supported by an RQ-7 Shadow and AC-130; a squad leader participates in a key leader engagement for the first time to disastrous outcomes. In all cases, the leader steps out of a virtual training environment and into a classroom where he guides his team through an after action review (AAR) that allows him to rewind, review, and truly understand the capabilities, and limitations, of his team and himself. The above scenario is still the ideal: a persistent, demanding training environment accessible from home station that provides joint and coalition context. While this ideal has not yet been achieved, it is within reach. Major strides were made toward this ideal for dismounted infantry units with the inception of the Army’s Dismounted Soldier Training System (DSTS) in 2012. However, the DSTS system suffered from a mismatch between trainee expectations and system capabilities. In response to the limitations of the system, the Army subsequently decided to downsize its DSTS inventory and transfer most of the remaining systems out of the active force. This paper focuses on gains in capability, usability and training transfer experienced with DSTS since 2011, analyzing feedback from multiple Services and nations across six mission types and multiple use cases. It provides an overview of four years of training transfer, systems feedback, and interoperability gains data spanning five experiments and over 200 participants, and the usability challenges which were recorded at every stage of the capability development. It offers recommended areas for future improvements, pitfalls to avoid, and describes future capabilities that could meet soldier expectations about training.