This study aims to identify, establish and discuss the potential problems associated with outsourcing military functions to private enterprises within the context of “grey-area” threats. This is of high relevance as essential parts of the Swedish armed forces (SAF) sea logistic chain are dependent on private shipping companies (PSC) as they do not possess these functions inhouse, and the “grey-area” in particular is a subject of great juridical uncertainty. By focusing on chartering and freighting outsourcing between PSCs and the SAF, the ambition is to identify certain risks, complications and difficulties for the operational capacity of the SAF, that may arise as a result of threatful situations within the grey-area.By conducting in-depth interviews with prominent personnel within both the SAF and PSCs, it has been possible to identify certain areas of complex issues and challenges necessary to address when entering into freighting agreements adequate for grey-area threats. In conclusion the study identified the following main problematic areas: ·      No guarantee from the state to ensure PSC assets when damaged by grey-area activity, puts increasing demand for good will between parties. This is problematic in the sense of becoming a normative relationship, and not substantial. ·      The SAF may find themselves in a disadvantageous position in terms of competences and resources when negotiating agreements.  ·      Lack of PSC involvement in defence planning leads to deficient understanding for SAF needs and demands. ·      PSCs as civilian corporations are more vulnerable to societal disturbances, which may lead to slow response in crisis-situations. ·      PSCs as a global industry risk (i) exploitation of free-market dynamics by antagonistic activity through foreign co-ownership and buyout, (ii) juridical limitations through PSCs using ships of foreign nations (flag), and (iii) shortage in manpower, as well as security threats to SAF interests may arise by PSCs using multinational crews. ·      Freighting between parties is a time-consuming process which may be problematic for quick response to grey-area threats.