Tunneling and Underground works are unequivocally subject to a diversity of inherent uncertainties associated with the geotechnical, hydro-geological and environmental regime that surrounds them. On many occasions, these uncertainties can provoke loss events of considerable consequences. The present contribution elaborates on losses that the insurance market has suffered in the recent years, following a construction failure event. These losses are being considered and analysed on a quantitative basis through evaluation of cost related data, with explicit discretization of the applied construction methodology and of the subsequent developed failure type since both of which are considered of major importance. Given the identified persistence and regularity of some loss-contributing factors, recommendations are provided on the basis of a proactive risk engineering management approach that are envisaged to reinforce the understanding of project risks and alleviate the incurred insurance cost.