Tax-loss harvesting and capital-loss guides for crypto and stocks.
Yes, options losses are generally deductible — but whether you're the buyer or the writer, and whether the position expired, was exercised, or was assigned, changes the holding period, the cost basis, and even the wash sale exposure. Here's the mechanics with worked examples.
Exercising incentive stock options can trigger the Alternative Minimum Tax on a paper gain that later evaporates. Here's how the AMT credit actually works, why it can take years to get that money back, and the three ways to handle an exercise before it happens to you.
Margin interest can be deducted as investment interest expense — but only up to your net investment income for the year, and a net capital loss doesn't count as income. Here's why the deduction often disappears in exactly the year you need it most.
Impermanent loss shows up in your liquidity pool balance long before it shows up on any tax form — and for most people, it never becomes deductible on its own. Here's the actual mechanic, the math behind why it happens, and how it gets folded into your capital gain or loss only when you withdraw.
Airdropped crypto is taxed as ordinary income the moment you can control it, based on what it's worth that day — not what it's worth when you eventually sell. If the token later craters, the loss you get back is capped at $3,000 a year. How the rule actually works, with a worked example.
The IRS's own Office of Chief Counsel ruled in 2025 that pig-butchering crypto scam losses can qualify as a deductible theft loss under Section 165(c)(2) — but only if you can show profit motive, and a nearly identical romance-scam loss can be fully disallowed. Here's the actual test, the forms, and the math.
Trader tax status and the Section 475(f) mark-to-market election can remove the $3,000 annual capital loss cap entirely — but qualifying is a facts-and-circumstances test, the trade-off is steep, and whether it even applies to crypto is genuinely unsettled.
NFT losses follow the same capital-loss rules as crypto or stock — sell or dispose of it to realize the loss, no deduction just for a floor price dropping. But two under-covered wrinkles change the math: the IRS's move to tax some NFT gains as collectibles, and the personal-use trap that can void the deduction entirely.
Give away a depreciated stock or crypto position to a family member and the built-in loss often can't be claimed by you or them — a quirk called the dual basis rule. How it works, the sell-first alternative that preserves the loss, and a worked example.
The advice to 'donate appreciated assets to charity' flips completely once a position is underwater. Donate a losing stock or coin directly and you forfeit the capital loss for good. Sell first, then donate the cash, and you keep both. The full comparison, a worked example, and the crypto-specific appraisal rule most people miss.
Losses inside a 401(k), traditional IRA, or Roth IRA generally can't be deducted on your tax return — and a 2025 law permanently closed the one narrow exception that used to exist. Here's how retirement-account losses actually work, compared to a taxable brokerage account.
When a margin or futures position gets force-closed, the IRS still treats it as a sale — you owe tax or claim a loss based on the liquidation price, not what you meant to exit at. How the gain or loss is actually calculated, and why the type of contract you were trading changes the tax rate.
The IRS treats crypto staking rewards as ordinary income the moment you can control them, then taxes any gain again when you sell — a two-event rule that's currently being challenged in federal court and in a pending bill. How the rule actually works, with a worked example.
The IRS's new Form 1099-DA is showing millions of crypto investors a taxable gain on coins they actually lost money on, because exchanges often don't know the real cost basis. Why it happens, and exactly what to do before the IRS notices a mismatch.
A $60,000 capital loss doesn't disappear if you can't use it all this year — but most people don't realize how the carryforward actually works, or plan for it. The multi-year math, with a worked example.
When a token is delisted, rug-pulled, or frozen in a bankrupt exchange, there's often no market left to sell into — so how do you actually realize the loss for tax purposes? The three different claims (capital loss, worthlessness, theft), why they're not interchangeable, and what proof each one needs.
The wash sale rule blocks stock investors from selling at a loss and immediately buying back in — but crypto has occupied a gray zone on this for years. Here's how that gray zone actually works, where it's changing, and what to verify before you use it.
Which lot counts as "sold" when you have crypto bought at different prices and times — and why picking the wrong accounting method can mean paying tax on a gain when you actually realized a loss.
A practical checklist of the transaction records to keep so you can substantiate capital losses at tax time, and why crypto makes this harder than it needs to be.
How realized crypto losses can offset gains and reduce a tax bill, explained in plain language — with what to check before assuming any of it applies to you.