IRS & California Tax Blog

Crypto Voluntary Disclosure: Should You Amend, Disclose, or Wait?
Kugelman Law

If you have unreported cryptocurrency income from past years, crypto voluntary disclosure is the set of paths for coming back into compliance before the IRS finds you first. There are really three choices: amend your returns, enter a formal IRS program, or wait. The right one depends almost entirely on a single question, whether your…

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What the IRS Knows About Your Coinbase History When You Get Letter 6174
Kugelman Law

Quick answer: Does Coinbase report to the IRS? Yes, and by the time a Letter 6174 lands in your mailbox, the IRS very likely already holds data about your exchange activity going back years. It gathers that information from tax forms the exchanges file, from court-ordered summonses that pulled historical account records, and now from…

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Streamlined vs. IRS Voluntary Disclosure: Which Path Fits Your Case
Kugelman Law

The choice between the streamlined procedures and the IRS Voluntary Disclosure Practice comes down to one question: was your failure to report foreign accounts non-willful or willful? Non-willful taxpayers generally use the streamlined program, which is cheaper and simpler. Taxpayers whose conduct may have been willful, and who therefore face potential criminal exposure, generally need…

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QSBS Stacking, Gifting, and the Section 1045 Rollover
Kugelman Law

QSBS stacking is how sophisticated founders and investors try to push the Qualified Small Business Stock benefit beyond a single exclusion cap. The exclusion under Section 1202 is limited per company, but that limit applies separately to each taxpayer who owns the stock. By spreading QSBS among family members or trusts before a sale, and…

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Crypto Scam Loss: Can You Amend to Claim a Theft Loss?
Kugelman Law

Quick answer: If you lost cryptocurrency to a scam and never claimed a crypto scam theft loss on the year it happened, you may be able to amend that return to claim it, and the deduction can be substantial. The rules are technical, and two points decide a lot: scam losses tied to an investment…

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Streamlined Filing Compliance Procedures: Who Qualifies and How They Work
Kugelman Law

The Streamlined Filing Compliance Procedures are the IRS’s main path back into compliance for taxpayers whose failure to report foreign accounts and income was non-willful. In exchange for filing three years of tax returns, six years of FBARs, and a certification that your conduct was non-willful, you resolve the back years at a reduced penalty:…

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Sold Crypto at a Loss? You Probably Still Had to Report It
Kugelman Law

Quick answer: One of the most common crypto tax mistakes is assuming that if you sold at a loss, you did not have to report it. You almost certainly did. Selling or exchanging cryptocurrency is a reportable event whether you made money or lost it, and leaving a loss off your return is exactly the…

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FBAR Penalties: Willful vs. Non-Willful and How to Reduce Them
Kugelman Law

FBAR penalties are among the harshest in the tax system, and the size of the penalty turns almost entirely on one question: whether your failure to file was non-willful or willful. Non-willful FBAR penalties run to roughly $16,500 per report for 2026, and after the Supreme Court’s decision in Bittner v. United States that penalty…

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California Source Income After You Move
Kugelman Law

California source income is income the state can tax because of where it was earned, not because of where you live. That is why leaving California does not always end your California tax bill. Even as a nonresident, you can owe California tax on equity compensation you earned while working in the state, on certain…

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QSBS Eligibility: Does Your Stock Qualify Under Section 1202?
Kugelman Law

QSBS eligibility is where the Qualified Small Business Stock benefit is won or lost. The exclusion under Section 1202 can erase federal tax on a large share of your gain, but only if the stock clears every requirement, both when it was issued and across your holding period. Many taxpayers assume they qualify because a…

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