Recent developments in the field of applied artificial intelligence have emphasised the necessity of interventions to mitigate cyber risks in contexts already affected by illicit interference in the free market. In this regard, it is appropriate to analyse the evolutionary scenario and the possible critical issues arising from the introduction of sophisticated systems that are continuously growing in their potential use capabilities, with a view to a market implementation that respects regulatory compliance criteria, also in light of recent interventions by the internal legislator to adapt to European regulations as well as the necessary management security requirements against external attacks and interference by criminal actors. Through an analysis of the actual legislation and the related proposals for future interventions, the paper aims at identifying the weaknesses and merits of an architecture aimed at mitigating the operational risk of the actors involved without neglecting critical findings that are functional to the improvement of the reference framework.