Recent policy changes in sustainability reporting, such as the ones related to the new European Directive on non-financial disclosure (2014/95/EU), the standards issued by the American Sustainability Accounting Standard Board (SASB), the G4 guidelines issued by the Global Sustainability Standard Board (GSSB), and the framework of the International Integrated Reporting Council (IIRC) stress the importance of extending the disclosure of ethical, social, and environmental risks within financial and social-environmental reporting. Institutional pressure has notably increased among organizations, in setting up risk management tools to understand sustainability risks within managerial and reporting practices. Given such institutional pressure, the corporate reaction in providing additional sustainability risk disclosure calls for attention and scrutiny. Therefore, this study aims at addressing such issues from an exploratory perspective. We based our analysis on a sample of large Italian organizations that issued sustainability disclosure in accordance with the Global Reporting Initiative (GRI), G4 guidelines, and we tested the relationship between their level of risk disclosure and other relevant variables. Consistently with the literature, we found that “experienced” sustainable reporters provide a significant volume of disclosure, and that disclosure quality on risk is positively influenced by their international presence and reporting experience. However, when accounting for specific risk-related areas of disclosure, only a few of them seem to adopt a managerial perspective linking strategy, risk metrics, and disclosure.