The Romanian legal environment on security interests has undergone significant changes during the last 15 years – turning from an outdated regime of nineteenth-century economics into an instrument allowing for flexible structuring of various security interests in a sound and bankable manner. There are still areas which show room for improvement, but the general trend is definitely positive. The chapter looks back at the 15 years which have passed since the adoption of Law 99/1999 and the ‘trial and error’ method that seems to have shaped security interests legislation. The chapter details the evolution of the legislation; in particular, it demonstrates the very modern Law 99/1999, which was also very pro-creditor. It purports that such a leap forward may have been perceived too creditor-friendly for the Romanian market, especially after Romania was hit severely by the financial crisis and credit crunch, and the new Civil Code has set back on some aspects, in particular that of private enforcement of security interests by secured creditors. On the other hand, the success of the Electronic Archive has not diminished and the benefits, especially in terms of costs, have been maintained. At the same time, Romania has embraced (via European Union membership) the financial collateral arrangements provisions, which will enable market players to operate under a set of rules which are well known and expected by international market players in this field.