Induced by a very unfavorable scenario of nontechnical losses (electricity theft), some electrical distribution companies in Brazil have moved from the traditional one meter per residence measurement process to a centralized multi-residences meter with two-way communication features, enabling both automatic reads and remote connect/disconnect of energy supplies. Those improvements can be seen as a natural transition toward an effective Smart grid, and have brought together the needs of a deep revision on regulatory procedures for the electrical meters evaluation conducted by the Brazilian Metrology Office. This paper shows that the increasing complexity from those new electrical grid equipments, particularly conveyed by additional software procedures, is a major issue and needs to be rapidly assimilated by metrological controls to avoid the appearance of stepping stones in the smart grid pathway. This paper aims to describe the whole set of relevant aspects revealed in this particular Brazilian experience, discussing the real scene and the respective challenges opposed.