Tokenization, Crypto and On-Chain Finance in Italy: What U.S. Investors and Businesses Should Know

Tokenization may significantly change the way financial assets, ownership rights and real-world assets are held, transferred and traded. For U.S. investors, entrepreneurs and businesses with interests in Italy, this evolution may also create new Italian tax, accounting and reporting obligations.

Digital assets are increasingly moving beyond the traditional cryptocurrency market and into the infrastructure of mainstream finance.

On September 22, 2026, Michael S. Selig, Chairman of the U.S. Commodity Futures Trading Commission, stated that financial markets should prepare for mass tokenization, on-chain finance and 24/7 trading.

According to the CFTC, tokenization may eventually affect multiple asset classes and could allow faster settlement, real-time collateral movements and new forms of financial market infrastructure.

This is no longer only about Bitcoin or speculative crypto trading.

The broader issue is the possible integration of tokenized securities, stablecoins, digital ownership rights and blockchain-based financial instruments into the traditional financial system.

What does asset tokenization mean?

In simplified terms, tokenization involves creating a digital representation of an asset or economic right using blockchain or distributed ledger technology.

Potential examples include:

• financial securities;
• bonds;
• receivables;
• shares or economic rights;
• real estate interests;
• investment funds;
• collateral;
• commodities;
• other real-world assets.

The important issue is not the token itself.

The real transformation lies in the possibility that the ownership, transfer, settlement and management of certain assets may progressively move onto digital and on-chain infrastructures.

Crypto assets are entering regulated financial markets

Another important signal comes from CME Group, one of the world's largest regulated derivatives marketplaces.

CME announced the planned launch, subject to regulatory review, of new futures on Bitcoin Cash and Uniswap beginning October 19, 2026.

The announcement expands an already significant institutional crypto derivatives market.

This development is relevant because it shows how instruments originally developed inside the crypto ecosystem are gradually becoming part of regulated traditional financial markets.

The long-term trend may therefore be broader than cryptocurrency trading itself.

Stablecoins and on-chain finance may become part of international business

For U.S. businesses operating internationally, stablecoins may eventually become particularly relevant.

They may be used for:

• cross-border payments;
• treasury management;
• settlement between businesses;
• digital investment structures;
• collateral management;
• international transfers.

For companies dealing with Italy, however, the technology does not eliminate the need to determine the correct Italian tax and accounting treatment.

A fast blockchain transaction can still generate very traditional questions:

How should it be recorded? How should it be valued? Is it taxable? Does it trigger reporting obligations?

Why this matters for U.S. individuals moving to Italy

The issue is especially important for U.S. citizens, executives, entrepreneurs and investors who become Italian tax residents.

A person moving from the United States to Italy may already own:

• U.S. brokerage accounts;
• company shares;
• RSUs or stock options;
• crypto assets;
• stablecoins;
• foreign bank accounts;
• digital wallets;
• DeFi investments;
• foreign companies or partnerships.

Once Italian tax residency begins, these assets may become relevant for Italian income taxation and foreign asset reporting.

Depending on the individual circumstances, Italian rules may require analysis of:

• foreign financial assets;
• crypto assets;
• capital gains;
• foreign-source income;
• foreign asset reporting;
• IVAFE;
• transfers between wallets or platforms;
• taxable events involving digital assets.

The U.S. tax system may continue to apply as well, particularly for U.S. citizens and green card holders.

For this reason, U.S.-Italy cases frequently require coordination between Italian and U.S. tax professionals.

Moving to Italy with crypto assets

Individuals relocating to Italy with substantial crypto or digital assets should ideally review their position before becoming Italian tax residents.

Important issues may include:

• acquisition cost documentation;
• transaction history;
• location and ownership of wallets;
• exchange statements;
• transfers between personal wallets;
• staking income;
• DeFi transactions;
• stablecoin holdings;
• prior disposals or conversions;
• foreign reporting requirements.

One of the most common practical problems in digital asset taxation is the lack of adequate historical documentation.

If transaction histories are incomplete, reconstructing the tax position several years later may become difficult and expensive.

Italian businesses using crypto or stablecoins

Italian companies and Italian subsidiaries of foreign groups may also increasingly face transactions involving digital assets.

Examples may include:

• receiving payments in crypto or stablecoins;
• holding digital assets on the balance sheet;
• using corporate wallets;
• making international payments through blockchain-based systems;
• investing in tokenized financial instruments;
• dealing with foreign digital asset platforms.

These transactions may require specific accounting treatment, documentation and internal controls.

The operational question is therefore not only whether a transaction is technologically possible.

The real question is whether the company can properly document, account for and defend the tax treatment of that transaction.

Tokenized real estate and investment structures

Another developing area is the tokenization of real-world assets, including real estate and investment rights.

For U.S. investors considering tokenized investments connected with Italy, it is essential to understand what the token legally represents.

A token may represent very different legal and tax positions depending on the structure.

For example, it may represent:

• direct ownership;
• a contractual right;
• an equity interest;
• a debt instrument;
• an interest in an investment vehicle;
• another type of financial entitlement.

The Italian tax treatment cannot therefore be determined solely by the fact that an asset is "tokenized".

The underlying legal and economic structure remains fundamental.

Cross-border tax issues will become increasingly important

Digital assets are inherently international.

An Italian tax resident may use:

• a U.S. exchange;
• a European exchange;
• a self-custody wallet;
• a decentralized protocol;
• multiple blockchain networks.

This creates tax and reporting questions that are often more complex than the technology itself.

For international investors, the key areas may include:

• tax residency;
• foreign asset reporting;
• capital gains;
• source of income;
• double taxation;
• valuation;
• documentation;
• succession planning;
• corporate ownership structures.

Studio Cavallari – Italian Tax Advisor

Studio Cavallari assists foreign individuals, international investors and companies with Italian tax, accounting and corporate matters.

Our work includes assistance with:

• Italian tax residency;
• inbound workers and expatriates;
• foreign asset reporting;
• Italian tax returns;
• crypto asset taxation;
• digital asset reporting;
• foreign investments;
• U.S.-Italy tax coordination;
• company formation in Italy;
• bookkeeping and accounting;
• VAT and corporate tax compliance;
• cross-border business structures.

As tokenization and digital finance develop, tax analysis will become increasingly important for individuals and businesses using crypto assets, stablecoins and tokenized investments.

For significant digital asset portfolios or cross-border situations, tax planning should generally be carried out before transactions or before a change of tax residency takes place.

Studio Cavallari – Italian Tax Advisor
Padua, Italy
Phone: +39 049 613584
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