Digitized mission support systems are currently being introduced in the military arena. The projected benefits include quicker, better informed, more efficient decision making by the teams using them; however, these claims are often made without appropriate scientific testing. A live operational field trial of a land warfare digital mission support system was observed, and an integrated framework of Human Factors methods was used to evaluate performance with the mission support system. The findings indicated that, as a corollary of various flaws associated with the digital system, decision making was found to be more difficult, more drawn out, and more susceptible to error. Rather than augment the decision-making process, in some cases these flaws were seen to create further decision-making requirements for users. In closing, the implications of this study and the wider naturalistic decision making literature for the design of digitized mission support systems are discussed.