The methodology today known as ‘qualitative’ has been used for centuries, although by different names (e.g., fieldwork, ethnography, etc.). Participant observation has been used over the centuries by anthropologists and sociologists who believed that the best way to gain insight into people’s attitudes, relations, etc. is to live with and observe them. Researching a military organization has proven to be extremely challenging. For example, it is very difficult to gain permission to enter such an organization and even harder to be given access to some specific units (special forces, military intelligence). Even after a researcher enters the military, they are confronted with yet another obstacle, namely, gaining the trust of the servicemen/servicewomen. The researcher’s presence itself presents another problem. It is almost impossible to ensure the ‘normal’ functioning of the military when there is an ‘intruder’ in its midst. This can be partially overcome if the researcher is a member of the military organization. However, this could also raise the issue of trust since other servicemen/women might have strong reservations about discussing their problems with someone who is part of the same institution due to the fear of such information being passed on to their superiors. This might be a problem, in particular, if the researcher has a higher rank. The question of the impartiality of a researcher who is also a member of a studied population also arises. A similar situation can be identified in the Slovenian Armed Forces (SAF ) where servicemen/women feel very reserved about consulting a military psychologist in case they need help since every consultation is marked in their personal files and, thus, might influence their future military career. The presence of civilian and neutral researchers coming from an outside research institution might solve some issues, yet at the same time it might provoke some other issues and dilemmas of researching military organizations. Some of the problems encountered when researching the SAF are described and further explored in this chapter.