This chapter focuses on the insurance issues arising from the use of unmanned aircraft, according to Italian and European regulations. In this context, the insurance issues are considered in the light, on one hand (European framework), of EU Regulation 2018/1139, which sets common rules in the field of civil aviation, supplemented by Delegated EU Regulation 2019/945 and Implementing EU Regulation 2019/947, and—on the other hand (Italian framework)—of ENAC UAS-IT 2021 Regulation. The European Regulations clarify that the operations with RPAS (Remotely Piloted Aircraft System) must be covered by adequate insurance, able to ensure that unmanned civil airborne traffic in European airspace is safe for people on the surface and in flight. The new European legislation is, in fact, based on the concept of risk of the operations. Likewise, in the Italian legal system, the ENAC Regulation requires an insurance coverage for civil liability risk, appropriate to the purpose and with maximum limits not lower than the minimum parameters set out in the table attached to Article 7 of Regulation (EC) 785/2004.