Transfer of Shareholdings and Contribution to a NewCo: Italian Supreme Court Confirms the Correct Tax Treatment
In judgments Nos. 19706 and 19709 of 2026, the Italian Supreme Court (Corte di Cassazione) reaffirmed that the transfer of all the shares in a company cannot automatically be recharacterised as a transfer of a business for registration tax purposes. In the first case, the Court confirmed that the transfer of 100% of a company’s shares retains its own distinct legal nature and remains subject to fixed registration tax, as it cannot be equated to a transfer of a business based on elements extraneous to the deed itself. In the second case, concerning the contribution of a business to a newly incorporated company followed by the transfer of all its shareholdings, the Supreme Court excluded the existence of an abuse of law, acknowledging the presence of genuine organisational and managerial reasons underlying the transaction. These rulings reaffirm the principle that taxpayers are free to choose, among lawful alternatives, the most tax-efficient structure, provided that the transaction is supported by genuine economic reasons.
Online Contracts: a simple Checkbox is not sufficient to approve unfair contract terms
By Order No. 20945/2026, the Italian Supreme Court clarified that, in contracts concluded online, merely ticking a checkbox is not sufficient to render unfair contract terms enforceable. The specific approval required under Article 1341 of the Italian Civil Code must be expressed through an electronic signature, including a simple electronic signature, provided that it enables the identification of the contracting party and unequivocally attributes consent to the individual unfair clause. For businesses operating through digital platforms, this decision requires a review of online contracting procedures by implementing separate acceptance mechanisms capable of constituting a valid electronic signature. The purpose is to ensure an informed and legally effective expression of consent while reducing the risk of challenges to the enforceability of contractual terms.
D&O Insurance Policies: no coverage where the Company Indemnifies Directors without a legal obligation
By Order No. 18458/2026, issued in the interest of the law, the Italian Supreme Court clarified the limits of Directors & Officers (D&O) liability insurance coverage. The Court held that any clause providing for reimbursement to a company of amounts voluntarily paid to indemnify a director against third-party claims is null and void where no such indemnification obligation arises by law or contract. In the absence of a legal or contractual obligation to indemnify, the insurable risk required under the rules governing indemnity insurance is lacking. The decision highlights the importance for companies of carefully reviewing the structure of their D&O insurance policies and ensuring that indemnification provisions comply with the principles of Italian law.
Artificial Intelligence: new corporate liability risks under Legislative Decree No. 231/2001
The Italian Council of Ministers has approved, on a preliminary basis, a draft legislative decree aimed at expanding corporate liability for offences committed through artificial intelligence systems. Among the key developments are the introduction of the new criminal offence of failure to adopt appropriate safety measures for high-risk AI systems and the inclusion, among the predicate offences under Legislative Decree No. 231/2001, of the unlawful dissemination of content generated or manipulated through artificial intelligence. Companies may therefore face significant financial penalties and disqualification measures where such offences are committed in their interest or to their benefit. Pending the final adoption of the decree, businesses are advised to assess the adequacy of their organisational models and internal procedures governing the use and control of AI systems.
Tax Payment notices: when a preliminary Tax irregularitynotice is not required
The First Instance Tax Court of Milan (Judgment No. 447/2026), in line with established Supreme Court case law, confirmed that a tax payment notice issued following the automated assessment procedure under Article 36-bis of Presidential Decree No. 600/1973 is valid even if it is not preceded by a preliminary tax irregularity notice, provided that the tax authorities merely calculate the amounts resulting from the tax return without amending the declared data. A prior communication is required only where uncertainties arise regarding material aspects of the tax return. The judgment also confirms the prevailing interpretation whereby taxpayers may still benefit from reduced penalties by paying the assessed amount within the statutory deadline following notification of the tax payment notice. Nonetheless, the issue remains subject to academic debate, as part of the legal scholarship considers that this interpretation weakens the procedural safeguards originally intended by the legislature to facilitate the early settlement of tax claims.
Business Transfers: liability for pre-existing debts remains subject to accounting records
By Order No. 20054/2026, the Italian Supreme Court reaffirmed that, in the event of a business transfer, the purchaser is jointly liable for debts arising before the transfer only where such liabilities are recorded in the mandatory accounting books, pursuant to Article 2560, paragraph 2, of the Italian Civil Code. Mere knowledge of the debt by the purchaser, even if proven, is not sufficient to establish joint liability. The Supreme Court further clarified that this limitation does not apply where there is no genuine distinction between the transferor and the transferee, such as in corporate transformations or transfers of sole proprietorships into single-member companies controlled by the same individual. Fraudulent or abusive transactions do not affect the application of the statutory rule but may instead be challenged through ordinary legal remedies, including avoidance actions and claims for damages.
Greenwhashing: new EU and stricter enforcement from 27 september 2026
As of 27 September 2026, the amendments to the Italian Consumer Code introduced by Legislative Decree No. 30/2026 will enter into force, strengthening the legal framework against greenwashing in implementation of the EU Directive “Empowering Consumers for the Green Transition”. The new rules prohibit the use of generic environmental claims that are not adequately substantiated, restrict sustainability labels to officially recognised or independently certified schemes, and prohibit describing products or activities as “carbon neutral” where such claims rely solely on carbon offsetting mechanisms. Future environmental commitments must also be supported by concrete, measurable and verifiable implementation plans. Businesses will bear the burden of substantiating their environmental claims and may face substantial financial penalties as well as significant reputational risks. It is therefore advisable to commence a comprehensive review of supporting documentation, advertising campaigns and commercial communications without delay.
Sustainable fashion: ban on the destruction of unsold goods for large companies
From 19 July 2026, Regulation (EU) 2026/296 will prohibit large companies from destroying unsold clothing, fashion accessories and footwear. The measure forms part of the European Union’s strategy for a circular economy and aims to reduce waste while promoting more sustainable production models. Affected companies will be required to prioritise alternative solutions such as reuse, donation, refurbishment or sale through dedicated distribution channels, including outlet stores. They will also be required to publish annual information regarding the products disposed of and the reasons for such disposal. Exceptions will only apply in strictly defined circumstances, including defective, hazardous, counterfeit or non-compliant products, provided that the relevant conditions are properly documented. The new regulatory framework will require businesses to review their inventory management processes and strengthen compliance with traceability and reporting obligations.