Italy is nowadays the only European country to have organized a head-on competition on its whole high speed railway (HSR) network. This paper discusses the issues of this new market structure for the Italian Rail Regulator, both in terms of regulatory design and economic regulation practices. Such HSR competition and regulation took place in a very specific and ambivalent context (including declining Italian railway demand, negative European macroeconomic environment), together with a new ambitious and innovating private competitor (NTV) and strong reactions from the incumbent (Trenitalia). The Italian Rail Regulator's interventions look like more or less a set of everyday life decisions and empirical trade-off than a duly achieved economic doctrine and policy. The level of access charges seems to be a strategic variable to enlarge the scope for profitable entry in Italy. However, this new context still does not answer the question whether HSR operators reach their economic equilibrium in open access competition.