Decree 231: Artificial Intelligence Enters the List of Predicate Offences
The draft law reforming Legislative Decree 231/2001, approved by the Council of Ministers to align national legislation with the EU AI Act and implement Law 132/2025, introduces the new Art. 25-vicies. The provision includes Art. 437-bis of the Italian Criminal Code among predicate offences, penalizing the failure to adopt technical security measures or human oversight for high-risk artificial intelligence systems where a specific danger exists. For breaches of security measures, pecuniary sanctions range from 600 to 1,000 shares, whereas for the unlawful dissemination of content generated or altered via AI (deepfakes, Art. 612-quater of the Criminal Code), fines range from 200 to 700 shares. In accordance with the principle of proportionality and to safeguard business continuity, targeted disqualifying sanctions apply (prohibition from contracting with the Public Administration, suspension of authorizations), excluding the suspension of business operations. Finally, liability for negligent omissions is restricted solely to cases of gross negligence.
Reform of 231 Corporate Liability and Harmonization of AI
The Council of Ministers approved the draft bill for the comprehensive overhaul of Legislative Decree 231/2001, aiming to reduce administrative burdens on companies and protect business operations and employees against potential employer misconduct. The reform enhances Organizational and Management Models as tools for compliance and transparency, adding a significant preventive component to the penal system. Concurrently, the draft legislative decree aligning national legislation with the EU Artificial Intelligence Regulation for policing activities and civil and criminal liability was approved. The measure establishes an integrated legal framework that eliminates automated procedural mechanisms and reaffirms the necessity of constant human oversight regarding technological outputs.
Human Oversight Must Always Be a Documented Process
The criminalization of offences linked to high-risk AI usage extends administrative criminal liability across the entire technological supply chain, placing a substantial burden on companies deploying such systems within operational processes (deployers). Because the duty of care/guarantor position cannot be contractually transferred to third-party suppliers, human oversight within the 231 Model must manifest as a tracked and documented operational process. Companies are required to audit sensitive algorithms, appoint supervisors with effective override authority, trace verification checks, and ensure continuous information flows to the Supervisory Board (OdV). Adherence to technical standards and certifications helps exclude gross negligence by the entity; however, mere formal compliance is insufficient to rule out liability if an economic advantage linked to cost savings on control measures or validation times is identified.
VAT Fraud: Automatic Denial of Input VAT Deduction Unlawful Without Proof of Knowledge
The First Instance Tax Justice Court of Padua (Ruling No. 123/2026) reaffirmed that the right to deduct input VAT cannot be denied to the purchaser based on mere presumptions or automated mechanisms. To deny deductions involving “at-risk” suppliers, the Tax Authority must prove with objective, grave, and precise evidence that the buyer knew or could have known of the fraudulent activity. Where the enterprise demonstrates that it acted with required professional diligence—by verifying accounting documentation and requesting the Single Tax Clearance Certificate (DURC)—its good faith cannot be compromised by subjecting it to investigative inquiries outside its scope of responsibility.
Extinguished Companies: Unappealed Tax Assessment Notice Renders Claim Final for Former Shareholder
In Order No. 24064/2026, the Court of Cassation ruled that the failure to timely appeal an assessment notice served on a former shareholder, but addressed to an extinguished company, renders the tax claim final against that shareholder as well. The ruling grants direct effect to the underlying tax assessment provided the shareholder was in office during the audited tax year. However, this decision highlights a strong conflict with the orientation of the Joint Sessions (Ruling No. 3625/2025), according to which shareholder liability under Art. 36 of D.P.R. 602/1973 requires an independent procedure stating the specific grounds for personal liability, rather than mere derivative service of the corporate assessment notice.
Tax-Exempt Generational Transfers via Effective Change of Control
The exemption from inheritance and gift tax provided by Art. 3, paragraph 4-ter of Legislative Decree 346/1990 for transfers of businesses and equity holdings to spouses and direct descendants applies on condition that corporate control under Art. 2359 of the Civil Code is acquired or consolidated, and retained for a period of no less than five years (holding period). Transferees must make a formal commitment to maintain control at the time of the inheritance declaration or gift deed; failure to comply results in the recovery of ordinary taxes, application of penalties (25%), and statutory late interest. In corporate restructurings executed via family holding companies (including under the controlled realization regime of Art. 177, paragraph 2 of the Consolidated Income Tax Act – TUIR) or transfers retaining usufruct rights for the parent, the Revenue Agency and the Court of Cassation condition the tax relief upon the actual transfer of control to the bare owners, disallowing the exemption if management powers and voting rights remain with the usufructuary.
Repayment of Shareholder Loans: Criminal Criteria in Insolvent Scenarios
In Ruling No. 31401/2026, the Court of Cassation defined the boundaries of criminal liability for repayments made to shareholder-directors near insolvency. The withdrawal does not constitute fraudulent bankruptcy by asset dissipation (bancarotta distrattiva) if the prior existence of a genuine loan agreement (mutuo) is proven, as the shareholder is settling a bona fide debt; provided other statutory elements are met, such conduct may instead constitute preferential bankruptcy (bancarotta preferenziale). Conversely, the return of capital contributions or transfers lacking strict documentary evidence (traceability, financial statements, corporate resolutions) constitutes an unlawful diversion of corporate assets.