Why Investors Struggle to File Their Taxes

Digital asset users are raising concerns about filing crypto taxes as the volume of on-chain activity continues to grow.

These issues come amid a regulatory shift marked by the adoption of the Crypto-Asset Reporting Framework (CARF) across various countries. This aims to address long-standing gaps in cryptocurrency tax oversight.

IRS Crypto Tax Reporting Requirements in the US

For context, the Internal Revenue Service (IRS) treats digital assets as property, requiring the reporting of income and capital gains from transactions, such as sales, service payments, staking, airdrops, and more.

It is worth noting that simply holding cryptocurrency does not result in a gain or loss and is therefore not subject to tax. Taxation occurs only when the asset is sold, and cash or another cryptocurrency is received. At that point, the gains are considered “realized,” creating a taxable event.

“Keep in mind that most income is subject to taxation. Failing to accurately report income may result in accrued interest and penalties,” the guidelines read.

For the 2025 tax year, the standard IRS filing deadline is April 15, 2026, unless the date falls on a weekend or holiday. Taxpayers may request an extension until October 15, 2026, but this extension applies only to filing, not to payment.

Investors Highlight Challenges in Filing Crypto Taxes Amid High-Volume Transactions

While tax guidance is quite clear, execution remains complex. For investors with high transaction volumes, reconciling activity across centralized exchanges, decentralized exchanges, bridges, liquidity pools, derivatives platforms, and multiple wallets has become a significant challenge.

Errors in transaction classification or cost basis calculation can materially affect reported gains and losses.

“The scary thing is, the burden of proof falls on the taxpayer to refute their low effort position…So if you don’t keep accurate records, you could get screwed,” a crypto tax service wrote.

These challenges are most evident among high-frequency traders. In one shared case, an investor known as “Crypto Safe” reported executing more than 17,000 transactions across multiple blockchains in 2025.

The user added that existing tax software could collect transaction histories but was unable to calculate taxes accurately without extensive manual review.

“So this year, I will simply pay tax on withdrawals at the bank, as it is impossible for me to calculate the capital gains on individual trades,” the post read.

According to the user, this approach could result in an estimated overpayment of $15,000 to $ 30,000 compared to the actual tax liability. This situation has drawn attention from other investors.

“I have overpaid every year since 2012,” another market watcher added.

Pseudonymous investor “Snooper” shared that filing crypto taxes, especially at high transaction volumes, requires advanced tax tools, familiarity with blockchain explorers, and manual data imports. Even with these tools, the process remains complex.

The case illustrates that proper compliance increasingly requires technical expertise beyond standard accounting practices.

Global Crypto Tax Reporting Enters a New Phase

Meanwhile, 2026 marked a major shift in global crypto tax regulation across many jurisdictions. As of January 1, 2026, 48 jurisdictions have implemented CARF.

This framework requires in-scope service providers to collect expanded customer data, verify users’ tax residency, and submit annual reports detailing account balances and transaction activity to domestic tax authorities.

That data will then be shared across borders under existing international information-exchange agreements. While the first automatic international exchanges of this information are scheduled for January 1, 2026, this date serves as the effective date for jurisdictions to implement the necessary legal frameworks and reporting systems.

The initiative includes the UK, Germany, France, Japan, South Korea, Brazil, and many EU nations. The United States, Canada, Australia, and Singapore are scheduled to join later.

Overall, 75 jurisdictions have committed to CARF. However, the move has attracted substantial criticism from the community.

“Crypto tax data collection has begun across 48 countries ahead of CARF 2027 implementation. Imagine paying tax on crypto the government doesn’t even print. This is a down side of regulation with all the amazing things it brought, Privacy in crypto is not what it used to be,” Brian Rose, Founder and Host of London Real, remarked.

These developments underline a widening gap between regulatory expectations and the practical ability of investors to comply. While governments are building reporting infrastructure, many investors continue to rely on tools that struggle to handle high-volume, multi-chain activity.

As tax policies tighten globally, high-frequency crypto users face growing pressure to develop sophisticated compliance workflows or risk inaccurate filings, higher tax costs, and potential disputes with tax authorities.

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