Soldiers in theater are confronted daily with complex, novel and uncertain conditions. This continual learning environment can be leveraged to quickly incorporate lessons learned into institutional training. The widespread availability of helmet-mounted and handheld cameras transforms this environment into a tremendous source of raw material from which to develop current, relevant training content. To fully leverage the training effectiveness of such content, Soldiers and Leaders must be equipped to create engaging and effective video training for just-in-time learning. This paper reports on the front-end analysis, skill and content selection, development, and empirical analysis of a framework for end-user production of video-based training. We describe a methodology through which the content of recorded task demonstrations can be augmented using annotations. We investigate this methodology by developing exemplar training products representative of the types of annotated videos that Soldiers and Leaders could produce, in domains selected during focus groups with Army Leaders including Counter-IED and Tactical Combat Casualty Care. Video content is annotated with narration, explanatory text, and images that serve to highlight essential features of task performance, contextualized with stories told by experienced Soldiers. Such "expert stories" provide novices with relevant cases to learn from and serve as an innovative form of annotation. Our empirical evaluation employs pre- and post-assessments using Soldiers (E1-E4) with varying backgrounds and experiences to assess the effects of different types of annotated training videos on subject matter expertise and situational judgment. Describing the process of producing these videos serves to illustrate the manner in which this technique might be used by Soldiers and illuminates issues associated with existing training needs and this mode of satisfying them.