Route (re-)planning requires many numerical computations to be made (e.g. time at destination, remaining range, distance to threats) in order to be able to assess feasibility and compare alternatives,. Nowadays, the required functions to perform these computations are an integral part of route planning tools, leaving the human operator in the role as a decision maker. Research into human decision making in the monetary domain shows that in certain situations, humans tend to be risk averse when it concerns potential gains and risk seeking when it concerns potential losses. The research described in this paper aims to determine to what extent these biases can be found in route-planning related decisions. An experiment has been conducted to compare decision making in the monetary domain with decision making in the military domain. The results concerning the monetary domain were mostly consistent with the expected biases. Especially risk aversion in decisions that imply potential gains showed up clearly in the data. In the military domain, the two most important findings were that decision making is dependent on many factors that do not play a role in monetary decisions. Participants' interpretations of different situations varied greatly, resulting in (close to) fifty-fifty distributions in their preferred answers. However, participants tended to agree more often in cases where the protection or saving of own troops was involved. In these situations, participants displayed risk-seeking behavior to prevent the loss of lives.