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Navigating crypto tax 1099 da: a guide for gamblers

Navigating Crypto Tax Changes | User Faces Challenges with 1099-DA

By

Liam Oโ€™Connor

Jan 8, 2026, 01:04 AM

2 minutes reading time

Illustration of a person calculating taxes with cryptocurrency symbols and a 1099-DA form

As taxpayers adjust to the new 1099-DA tax requirement, a user grappling with crypto transactions specifically for gambling is raising questions. In a unique case, they only sold a small amount of Bitcoin and made no profits from their gaming activities this year.

The Situation Explained

The user reports utilizing crypto assets only for gambling, amounting to approximately $1,000, with only a single Bitcoin sale worth $17. Thereโ€™s uncertainty on how to report these transactions correctly, given that most funds transferred to the gambling site were likely converted into tokens, complicating the tax implications.

"Youโ€™d tag those sends as 'spend,' assuming the crypto deposit was turned into some form of onsite coin," noted one commentator.

Key Points from the Discussion

Comments from various forums highlight three main themes:

  1. Transaction Reporting: Many users emphasize that each withdrawal to the gambling site counts as a sale or disposal. Thus, each action must be reported accurately in tax software.

  2. Cost Basis Calculation: It's essential to determine the fair market value (FMV) of the crypto at the time of receiving tokens, particularly if the Bitcoin was earned through gambling.

  3. Loss Deductions: The user will need to address how gambling losses can only be deducted to the extent of gambling winnings, which in this instance, were non-existent.

Seeking Clarity on Tax Software Usage

The confusion continues about how to use crypto tax software. The user suggests importing transaction histories from platforms like Cash App to assist in calculations. Another user confirms that this is the correct approach, adding a note about tagging specific transactions effectively.

โ€œEvery 'withdrawal' you mention counts as a sale,โ€ warned another commentator, stressing the importance of meticulous record-keeping.

Key Takeaways

  • โ–ฝ Each crypto withdrawal to the gambling site is considered a sale.

  • โ˜… Accurately report cost basis related to game tokens earned.

  • ๐Ÿ”น Losses from crypto used in gambling are deductible only against winnings.

With the tax deadline approaching, those in similar situations must ensure they understand the nuances of crypto tax regulations to avoid complications. What steps will they take to ensure compliance?

What Lies Ahead for Crypto Taxation in Gambling?

There's a strong chance that as crypto gambling grows, tax regulators will tighten their scrutiny on transactions. Experts estimate around 70% of taxpayers dealing with crypto might struggle to report accurately, given the complexity of regulations. This confusion could prompt more calls for clearer rules from the IRS. As awareness of crypto taxation increases, platforms may improve their reporting features, easing the burden on taxpayers. However, non-compliance risk could lead to more audits and penalties, placing further responsibility on individuals to keep detailed records of their transactions and maintain transparency.

The Unexpected Nature of Historical Taxation

In the 1920s, Prohibition turned the alcohol trade into an underground market, forcing many to misreport or hide their earnings, similar to the dilemmas faced with crypto today. Just as speakeasies became a haven for hidden revenue, players using crypto for gambling often must navigate complex reporting environments to avoid missteps. This past scenario illustrates how evolving regulations can create a dual atmosphere of opportunity and risk, showing that the nuances of compliance often reflect a historical struggle within our financial systems.