The article offers an analysis of the aviation product liability regime and related insurance issues as developed in Italy through a comparison with US and UK insurance practice. A comparison is made between the US ABC (Aircraft Builders Council Inc.) form, the London Aircraft Insurance Policy form AVN1D with the Italian form. The analysis also considers how the new technologies applied to aircraft and air transport infrastructure (such as ATM, ATN etc.) have influenced the product liability insurance policies. The current allocation of risks and liabilities among the various operators of the aviation sector could be changed by the implementation of the EU Single European Sky Programme. Moreover, the improvement of anti-collision devices should increase safety and lead to review the allocation of risks among the ATM stakeholders and consequently change the allocation of responsibility and the relevant insurance obligations. This is what occurred in recent cases examined in the article.