Hindsight is 20/20, but when money is on the line, being prepared can give investors better foresight. Just over a year and a half ago, Investopedia reported on the panic among many crypto investors who’d found themselves on the wrong side of the taxman. The article read, “Online forums like Reddit are abuzz with posts citing possible scenarios by worried investors about pending tax liabilities for their past dealings in cryptocoins, which may now leave them poorer.”

As Bitcoin’s 

BTC

$22,937

 price soars and investors flock to crypto to cash in, legislators and regulators around the world are taking notice. Most recently, the Organisation for Economic Co-operation and Development announced a plan to release a ubiquitous tax standard for its member states, partly intended to curb base erosion and profit shifting. Although announcements like these serve as positive signs of intergovernmental collaboration, economic unity and progress, to the average investor, they feel rather distant. Yet it is crucial for investors in the United States to understand the digital asset tax regulations because, in some cases, it may mean the difference between prosperity and five years in prison with fines up to $250,000.

Related: Parents, it’s time for ‘the talk’: Did your kid trade crypto in 2020?

A handful of libertarian, crypto torchbearers might be inclined to believe that the built-in anonymity privileges of blockchain may save them from government scrutiny, but after all, the Internal Revenue Service isn’t quick to let go of these matters.

The U.S. tax code and crypto

Digital currencies and tokenized assets tend to be a mixed bag under the U.S. tax code. Many investors think of Bitcoin as a digital currency, like fiat currencies used regularly by consumers to buy goods. However, under the U.S. tax code, Bitcoin is actually considered “property” and is taxed under capital gains tax when either sold or used to purchase items or transferred for other digital currencies, such as trading Bitcoin for Ether 

ETH

$1,637

. For example, purchasing a house with Bitcoin in the U.S. would trigger a taxable event on capital gains, and the exchange of Bitcoin for any other type of asset is considered a sale in the same way you might sell security like a stock.

Related: Crypto taxes, reporting and tax audits in 2021

It’s difficult to pinpoint why Bitcoin is classified differently from fiat currencies, but precedent in how Bitcoin is utilized by investors may tell us the answer. The IRS likely recognizes Bitcoin as a property asset because the popular crypto asset serves most users as an investment utility and not as a functional currency in the same way the fiat U.S. dollar does. More importantly, because these types of assets are not issued by a central bank, the U.S. government will not recognize them as such until further notice. Understanding crypto taxation also means digging into the little details.

Unlike centralized financial systems, decentralized systems require investors to take a far more active role in diligently tracking their investments from the moment of purchase to sale or exchange for commodities.

At the most basic level, the onus falls more on the investor to track the purchase date, purchase price and what was received in exchange for the Bitcoin in the case of a sale. In contrast, investment history in traditional, non-digital assets, such as stocks or commodities, is fairly easy to track because of the diligent records that brokerages maintain for clients and how readily accessible they are.

Crypto investments and taxation

Basics aside, there is one area in particular in which many accredited investors miss the mark.

Crypto hedge funds are reputed for offering lucrative crypto opportunities. While some crypto hedge funds are considered risky due to questions about crypto-market liquidity, they can be the better route to invest instead of buying individual units of Bitcoin. And as of late, they have proven themselves increasingly popular over the last year. According to Big Four audit firm PricewaterhouseCoopers, assets under management with crypto hedge funds rose from $1 billion in value in 2018 to over $2 billion in value in 2019. Despite piquing the interest of investors, buyers beware.

Compared to traditional assets, when onboarding investors for crypto assets, it’s a whole different ball game. Unlike traditional assets, it’s imperative that digital asset hedge funds ask deeper questions about tax considerations. Some questions regarding crypto investments should include: What kind of property is cryptocurrency x? or Can staking assets on proof-of-stake networks, which offer rewards for staking, be classified as unique income? These are just the basics, but questions like these can easily slip the mind when in the moment and can trigger unintended tax events.

On the other hand, when joining a hedge fund, it’s standard procedure to sign a standard legal entity fund structure, which is often as lengthy as 500 pages. Included are taxation clauses in the contract that explain the implications of investing with the fund. But with hundreds of pages of details, investors may not pay close attention to the little details, inadvertently putting them at serious risk of conflict with the IRS at a later juncture. That’s where a tax advisor should come in, who is accustomed to a more passive role.

Because of crypto’s unique properties, the tax advisor’s role has to become more active rather than passive, as it usually is. Rather than take a backseat, tax advisors should be summoned to provide consultation on investments before they’re undertaken and play a proactive role in educating investors every step of the way. As a result, investors would find themselves better prepared to provide a comprehensive and abiding tax return, rather than find themselves on the short end of the stick, playing catch up with the IRS.

When the taxman comes knocking, it’s better to be safe than sorry and know the regulations; otherwise, the consequences could be much graver. More importantly, the tax advisor must be in the passenger seat, not the back seat, when investors sign on the dotted line.

The views, thoughts and opinions expressed here are the author’s alone and do not necessarily reflect or represent the views and opinions of Cointelegraph.