The Tactical Action Officer on board a U.S. Navy Cruiser, Destroyer, or Frigate is responsible for the operation of the entire watch team manning the ship’s command center. Responsibilities include tactical decision-making, console operation, communications, and oversight of a variety of watchstander responsibilities in air, surface, and subsurface warfare areas. In previous work the PORTS TAO ITS, an Intelligent Tutoring System (ITS) for the instruction of Tactical Action Officers (TAOs) was developed to support training at the Surface Warfare Officers School. The system was built on the PC-based Openarchitecture Reconfigurable Training System (PORTS). This paper describes a novel extension of the PORTS ITS, where it is integrated with the popular Second Life 3D virtual world. In this integration, the TAO logs on as an avatar in Second Life (SL) and interacts with a number of computer-controlled objects that take on the roles of the TAO’s teammates. TAOs rely on the same mechanism to communicate with the simulated teammates in SL as they would to communicate with other human players. That is, the TAO speaks to these simulated teammates using the chat window built into SL and sees their replies and comments in the chat window as well. We provide both a high-level overview of the integration process as well as the details of integrating a deployed training system with the Second Life virtual world. Additionally, this paper presents “food for thought” on how recent advances in technology and social connectivity can be applied to military training domains and outlines proposed future work based on this integration.