In this dissertation, trade-off moral decision-making was examined through three experiments using military contexts, specifically RPA or related Intelligence operations. The first investigation expanded upon previous work done by Christen et al. (2020; Zenk, 2018) and introduced an updated RPA simulation which added physiological and expression measures as well as an active-choice paradigm and a varied order of missions, which would allow us to extend the conclusions of earlier research. The second and third investigations used a new paradigm involving militaristic dilemmas wherein participants took on the role of an intelligence officer. One experiment had participants approve a neutralization opportunity based on the deviant background of known targets, while the other had participants approve this opportunity based on variations in the demographics of innocent casualties (i.e. age and nationality).For the updated RPA simulation investigation, results indicated that the order in which missions were presented had an effect on overall moral decision-making choices, which was a concern in the original investigation. In addition, the influence of the active-choice paradigm was limited to instances where the non-redirect (non-utilitarian) choice was active. In this case, fewer than normal participants elected this choice even decision dilemma became more personal. This outcome was different from what is often found in Trolleyology research: namely, when moral decisions become more personal, more non-utilitarian choices are made.The two intelligence officer experiments showed that moral decisions are, indeed, affected by casualty numbers and the demographics of both targets and civilian casualties. First, the larger the number of civilian casualties, the less likely decision-makers are to make the choice to neutralize a target. Additionally, the higher threat perceived from a target, the more likely it is for a participant to authorize target neutralization, even as casualty number changes. Differences in decision-making also occurred as civilian demographics changed, most notably such that less information given about a casualty led to higher likelihood of neutralizing the target.Overall, these studies are important steps toward the creation of more in-depth simulations which are needed to better understand moral decision-making in a remote warfare context. Moreover, this research indicates that the common-dual-process explanations for Trolleyology outcomes must be modified to include a context-dependent component.