The boundaries of limitation of liability and indemnity clauses constitute an important longlasting debate in private law. In Civil Law countries, they find their origin in the banning of the agreement to waive liability for future willful misconduct as provided in roman law. However, this legacy does not reflect integrally the solutions given by Roman jurists, for whom the unbending standardized structure of the contract was regarded as the seminal threshold and which flexibilization among the centuries led to the limitations of willful misconduct, good faith, good uses and public law. In the following lines we analyze this evolution by using a legal systems perspective in order to identify new and apposite interpretations to the current issues on this matter in modern law and, as we will verify in the second part of this paper, are strongly related to the modification of standardized contracts’ content.