In this lesson
- Two Words That Sound Like They're Not for You
- What "Harvesting" Means, and the Machinery Underneath It
- The Move Nobody Tells You About: The 0% Capital-Gains Bracket
- Strategy Isn't Just for the Rich — and the Catch to Respect
- The Other Direction: Harvesting a Loss to Cut This Year's Bill
- The Rule That Guards the Loss: Wash Sales
- Choosing Which Shares You Sell: Specific-Identification Lots
- Nudging Past the One-Year Line: Holding-Period Management
- Crypto's Open Door: No Wash-Sale Rule (Yet)
- Reading a Harvesting Worksheet: Form 8949 & Schedule D
- Audit & Scam Watch: Where Harvesting Goes Wrong
- If This Already Happened to You
- Where to Get Help — the Harvesting Recourse Stack
- The Questions Almost Everyone Asks
- Check Yourself: Model Your Own Harvest
- Glossary — the Words You Now Own
Capital-Gain & Tax-Loss Harvesting
Two legal, deliberate moves that turn an ordinary brokerage account into a tax tool: harvest a long-term gain in the 0% bracket to reset your basis at no cost, and harvest a loss to cut this year's bill — both while staying fully invested, and without ever tripping the wash-sale rule.
What you'll learn
- Get past the idea that harvesting is a rich-person trick or a way to get in trouble — see that a gain harvest is a legal basis reset and a loss harvest is a legal loss offset, both explicitly built into the tax code
- Realize a long-term gain in the 0% capital-gains bracket and pay literally $0 in federal tax on it — and watch a modest-income filer (Nadia, on $58,000) do exactly that
- Harvest a loss to offset your realized gains and up to $3,000 of ordinary income, carry the rest forward forever, and cut the 3.8% Net Investment Income Tax at the same time
- Stay invested the whole time by buying a replacement that is not "substantially identical" — the move that keeps you in the market while the loss counts
- Understand the wash-sale rule cold: the 61-day window, and the four quiet ways people blow it — a repurchase in an IRA (where the loss is lost forever), a spouse's account, an auto-reinvested dividend, and a same-account rebuy
- Choose exactly which shares you sell using specific-identification lots — the difference between an $11,000 gain and a $6,000 loss on the very same sale
- Nudge a sale past the one-year line so a short-term gain taxed at ordinary rates becomes a long-term gain taxed at 15% — holding-period management
- Know why crypto has no wash-sale rule (yet) for 2026, and spot the harvesting scams — wash-sale violations, over-promising "harvesting services," and fake-loss schemes — plus the one rule that protects you and where to get help
Two Words That Sound Like They're Not for You
Lesson 30, Level 300 Optimization: Capital-Gain and Tax-Loss Harvesting — two legal, deliberate moves that turn an ordinary brokerage account into a tax tool. By the end you can realize a long-term gain in the 0% bracket at zero federal tax, harvest a loss to cancel gains and up to $3,000 of ordinary income while carrying the rest forward, stay clear of the wash-sale rule and its four quiet traps, choose which shares you sell with specific identification, nudge a gain past the one-year line, and spot the harvesting scams — including crypto's current lack of a wash-sale rule. The lesson follows three people: Priya and Raj, a higher-income couple loss-harvesting at scale; Nadia, on $58,000, harvesting a gain at 0%; and Chad, a crypto trader.
"Tax-loss harvesting." "Gain harvesting." The words sound like something a private wealth manager does for people with a comma or two more than you in their account — or worse, like a clever-sounding maneuver that gets ordinary people audited. Both fears are common, and both are wrong, and this lesson exists to replace them with something you can actually use. Here is the honest frame before we teach a single number: harvesting is not a loophole and it is not a gray area. It is two ordinary, fully legal moves the tax code openly invites, and the more surprising one — realizing a gain and paying zero tax on it — is available precisely to people with modest incomes, not just the wealthy.
Let's name the two moves plainly, because once you see them side by side the fear drains out. The first is tax-loss harvesting: you sell an investment that's worth less than you paid, which creates a capital loss, and that loss cancels out gains you owe tax on (and even a slice of your ordinary income). You don't have to leave the market to do it — you buy something similar back. The second is gain harvesting: in a year when your income is low enough, you deliberately sell an investment that has gone *up*, realize the gain, and pay tax on it at the 0% long-term capital-gains rate — yes, a real 0% — then buy it right back at the new, higher price. You didn't owe a cent, and you permanently raised your cost basis so a future sale is smaller. One move harvests a loss to cut this year's bill; the other harvests a gain at no cost to shrink a future one.
This is the strategy lesson: how and when to deliberately realize gains and losses to pay less tax, legally. It is not a re-teaching of how capital gains work mechanically — short vs. long-term, basis, the wash-sale rule, the $3,000 limit, carryovers — that's the investor mechanics lesson, and we'll recap just enough to make the strategy land. It is not about crypto specifics (that's its own lesson, and we'll point there), and it is not general tax planning (that's the planning lesson). Everything here is education, not personalized advice: whether a specific harvest is right for you depends on your whole picture, and for a large portfolio a professional earns their fee.
We'll learn this through three of our filers, each carrying a different piece. Priya and Raj Malhotra — a dual-income Seattle couple earning over $275,000 with a real brokerage account — lead the loss-harvesting story, because their higher income is exactly where a harvested loss saves the most. Nadia Okonkwo, the 26-year-old marketing coordinator in Columbus earning $58,000, carries the move that proves this isn't only for the wealthy: she'll realize a gain and pay $0 federal tax on it. And Chad Molina, a crypto trader in Denver, shows the one place the wash-sale rule doesn't reach — yet. By the end you'll be able to look at your own account in a down market, or in a low-income year, and know which harvest is yours — and how to make it without tripping the one rule that can undo it all.
What "Harvesting" Means, and the Machinery Underneath It
The word borrows from farming on purpose: you let something grow, and then, at the right moment, you deliberately gather it in. In investing, harvesting means intentionally triggering a taxable event — a sale — not because you need the money or want out of the investment, but because the *tax result* of selling right now is valuable. You then usually get right back into a very similar position, so your money stays invested. The whole art is in the timing and in staying inside the rules while you do it.
To use the two moves you only need a handful of ideas you've met before, so here is the fast recap — the machinery, not the full course. A capital gain is the profit when you sell an investment for more than your basis (what you paid, adjusted for things like reinvested dividends); a capital loss is the opposite. Hold the investment more than one year and the result is long-term — taxed at the gentle 0%, 15%, or 20% rates; hold it one year or less and it's short-term — taxed at your ordinary income rates, the same as wages. When you have both, they net against each other: losses first cancel gains of the same type, then across types, and if a net loss remains, up to $3,000 of it comes off your ordinary income, with anything left carried forward to future years. The wash-sale rule polices one thing — it stops you from claiming a loss if you rebuy the same investment too quickly. And the 3.8% Net Investment Income Tax (NIIT) is an extra tax higher earners pay on investment income. That's the toolbox. Every strategy below is just a clever arrangement of those parts.
The wash-sale rule only ever restricts LOSSES. It has nothing to say about gains. That single asymmetry is why gain harvesting lets you sell and instantly rebuy with no waiting period, while loss harvesting forces you to be careful about what — and when — you buy back. Keep it in your pocket; it explains half of what follows.
A side-by-side map of the two harvesting moves. On the left, harvesting a gain: in a low-enough-income year, sell an appreciated long-term holding; the gain lands in the 0% bracket so you pay zero federal tax; buy it right back with no waiting because the wash-sale rule ignores gains; and your cost basis resets upward so a future sale is smaller. On the right, harvesting a loss: sell a position that's down to book a real capital loss; the loss cancels your realized gains and then up to $3,000 of ordinary income; buy a not-substantially-identical replacement so you stay invested; and any leftover loss carries forward to future years forever. A banner notes that the wash-sale rule guards only the loss side — it never restricts gains.
Notice what the map shows: the two moves point in opposite directions but rhyme. A gain harvest deliberately *pays* tax — at a 0% rate, so "pays" means nothing — to step your basis *up*. A loss harvest deliberately *books* a loss to pull your tax *down*. In both, you end the day still invested in essentially the same thing. The rest of the lesson is these two columns, one at a time, with the wash-sale rule standing guard over the right-hand one.
The Move Nobody Tells You About: The 0% Capital-Gains Bracket
Start with the fact that disarms the "only for the rich" fear, because it's genuinely startling the first time you meet it: there is a 0% federal tax rate on long-term capital gains, and it is not a rounding trick or a temporary promotion. It is a permanent, built-in bracket, and it exists specifically for people with lower and middle incomes. If your total taxable income is modest enough, you can sell a long-held, appreciated investment, realize the gain, and owe the federal government exactly nothing on it. Most people go their whole lives without knowing the bracket is there, which is the real tragedy — it's a free basis reset, and it goes unclaimed.
For tax year 2026, the long-term capital-gains rates work in three bands, keyed to your taxable income (that's your income after your standard or itemized deduction — an important detail we'll use in a moment). The exact 2026 breakpoints, verified against the IRS's official inflation-adjustment figures (Revenue Procedure 2025-32), are:
| Filing status | 0% rate — taxable income up to | 15% rate — up to | 20% rate — above |
|---|---|---|---|
| Single | $49,450 | $545,500 | $545,500 |
| Married filing jointly | $98,900 | $613,700 | $613,700 |
| Head of household | $66,200 | $579,600 | $579,600 |
| Married filing separately | $49,450 | $306,850 | $306,850 |
Now the crucial mechanic that makes the 0% bracket usable, and that trips up almost everyone the first time — stacking. Your ordinary income (wages, interest, short-term gains) is counted *first* and fills the brackets from the bottom. Your long-term gains and qualified dividends are then stacked on top of that, and they get the 0% rate only for the portion that still falls below the 0% breakpoint. So the amount you can harvest at 0% isn't the breakpoint itself — it's the breakpoint minus the ordinary taxable income you already have. That leftover space is your "0% room." Fill it with long-term gains and they're taxed at nothing; go past it and the overflow is taxed at 15%. Let's put a real person in it.
Nadia's 0% room, to the dollar
Nadia earns $58,000 at one W-2 job. From her foundation return we know the numbers cold: her total income is $58,180 (wages plus $180 of bank interest), she subtracts $900 of student-loan interest to reach an adjusted gross income of $57,280, and after the 2026 single standard deduction of $16,100 her ordinary taxable income is $41,180. That $41,180 is what fills her brackets first. The single 0% capital-gains breakpoint for 2026 is $49,450. So her 0% room is:
Nadia's 0% harvesting room
$49,450 (0% breakpoint) − $41,180 (ordinary taxable income) = $8,270
Nadia can realize up to $8,270 of net long-term capital gain and pay $0 federal tax on it — the gain stacks from $41,180 up to exactly $49,450, entirely inside the 0% band.
Sit with that. Nadia is not wealthy, not retired, not in some special year — she's a 26-year-old on an ordinary salary, and she still has $8,270 of room to realize gains at a 0% federal rate. Say she owns an index-fund lot she bought years ago for $12,000 that's now worth $20,270 — an $8,270 long-term gain sitting there unrealized. She sells the whole lot. The $8,270 gain stacks on top of her $41,180 and lands right at the $49,450 ceiling, so every dollar of it is taxed at 0%. Her total federal tax for the year stays exactly $4,694 — the same as if she'd never sold. She realized $8,270 of profit and her tax bill did not move by a single dollar.
A horizontal bar showing how Nadia's income stacks into the 2026 long-term capital-gains brackets. Her $41,180 of ordinary taxable income fills the bottom of the 0% zone. Her $8,270 long-term gain stacks on top of it, rising from $41,180 to exactly $49,450 — the single-filer 0% breakpoint for 2026 — so the entire gain is taxed at 0% and costs her nothing. Above $49,450 the 15% zone begins, but her income stops right at the line, so she never reaches it. Her 0% room, the breakpoint minus her ordinary income, is exactly $8,270, and she fills it completely. Realizing the gain leaves her total federal tax unchanged at $4,694.
Here's why she'd bother, since she didn't need the cash: the instant she sells, she can buy the same fund right back — the wash-sale rule doesn't restrict gains, remember — and her new basis resets up to $20,270. She's now holding the same investment, but the government has, in effect, blessed $8,270 of past growth as already-taxed (at 0%). If that fund keeps growing and she sells it years later in a year when she's in the 15% bracket, she'll owe tax on $8,270 *less* gain — a future saving of about 15% × $8,270 ≈ $1,240, bought today for free. Gain harvesting is quietly one of the best deals in the tax code, and it's aimed squarely at people like Nadia.
The 0% rate is a ceiling, not a slope. If Nadia got greedy and realized $12,000 of gain instead of $8,270, the first $8,270 would still be 0%, but the $3,730 that pokes above the $49,450 line would be taxed at 15% — about $560. The gain that fits in the room is free; the gain above it is not. So the discipline of gain harvesting is filling the room precisely, not blowing past it. Software and your own math both let you land it to the dollar.
Strategy Isn't Just for the Rich — and the Catch to Respect
Nadia's story makes the democratizing point, so let's say it directly: the 0% gain harvest is most powerful for people with *lower* incomes, because the lower your ordinary income, the more 0% room you have. A person between jobs, a graduate student, someone taking unpaid leave, an early retiree living off savings before pensions and Social Security kick in, a business owner in a lean year — these are the people with the *most* room, sometimes tens of thousands of dollars of it. Where a high earner has zero 0% room (their ordinary income already blows past the breakpoint), a modest-income filer can reset the basis on a big chunk of a portfolio at no cost. The wealthy get the headlines; the 0% bracket belongs to everyone else.
Imagine Nadia takes a year to go back to school and her taxable income drops to, say, $20,000. Now her 0% room is $49,450 − $20,000 = $29,450 — more than three times as much gain she can reset at zero tax. This is why the classic playbook says: a low-income year isn't just something to survive, it's a harvesting opportunity. Retirees living in the gap between leaving work and starting Social Security often harvest gains for several years at 0%, permanently lowering the tax on a lifetime of investing.
But an honest strategy names its catch, and gain harvesting has one worth respecting: a gain taxed at 0% is still income for every other purpose. Realizing it raises your adjusted gross income and your "modified" AGI, even though the tax on it is zero. That higher AGI can quietly cost you elsewhere — it can shrink an Affordable Care Act health-insurance subsidy, raise a retiree's Medicare premiums (the IRMAA surcharge), increase how much of your Social Security is taxable, tip you out of an income-based phase-out, or nudge a college financial-aid formula. None of these undo the 0% rate on the gain itself, but they mean a harvest is a decision to weigh, not a reflex. The move is real and it's free of *income tax*; just check that it isn't quietly moving something else.
Two smaller cautions round it out. First, your state may still tax the gain even when the federal rate is 0% — most states tax capital gains as ordinary income, and a few (like Washington, where Priya and Raj live) have their own capital-gains levy on large gains; "0% federal" is not "0% everywhere." Second, gain harvesting only helps if you actually *have* an appreciated long-term holding in a taxable brokerage account — gains inside an IRA or 401(k) are already tax-deferred, so there's nothing to harvest there. With those checks made, the move is clean: fill the room, rebuy, reset the basis, owe nothing.
The Other Direction: Harvesting a Loss to Cut This Year's Bill
Now the move most people have at least heard of, and the one that fits Priya and Raj. Tax-loss harvesting is selling an investment that's worth less than you paid, on purpose, to turn a paper loss into a *realized* loss the tax code will use for you. A paper loss — a holding that's down but that you still own — does nothing on your tax return; the market can cut your position in half and, until you sell, the IRS neither knows nor cares. The instant you sell, that loss becomes a tool. And here's the reframe that dissolves the "this feels like giving up" discomfort: you are not abandoning the investment or admitting defeat. You are converting a temporary dip into a permanent tax benefit, and then — this is the key — getting right back into the market so you don't miss the recovery.
What does a realized loss actually do? It works through the netting order you met in the recap, in a specific sequence. First, losses cancel gains of the same character: long-term losses first offset long-term gains, short-term losses offset short-term gains. Then the two nets combine, so a leftover loss of one type can cancel a gain of the other. If, after all that, you still have a net loss, up to $3,000 of it comes off your ordinary income this year ($1,500 if you're married filing separately) — a cap that has stood unchanged for decades and has never been adjusted for inflation. And whatever loss is *still* left doesn't vanish: it carries forward indefinitely, keeping its short- or long-term character, ready to cancel gains or take another $3,000 bite next year, and the year after, until it's used up. Individuals can only carry losses *forward*, never back to a past year.
Priya and Raj harvest a loss — the worked numbers
Priya (a software engineer, $185,000 plus equity) and Raj (a consultant, about $90,000) file jointly with a combined income over $275,000 and a real taxable brokerage account. In 2026 they rebalanced and, in doing so, sold some long-held winners, booking $40,000 of long-term capital gains they'll owe tax on. They also hold a concentrated position — a sector fund they bought near a peak — that is now deep underwater, sitting on a $55,000 long-term paper loss. Harvesting is almost too tidy here. They sell the losing fund, realizing the $55,000 loss, and net it against everything:
| Step | What happens | Amount |
|---|---|---|
| Realized long-term gains (rebalancing) | Winners they sold — taxable | +$40,000 |
| Harvested long-term loss (the sector fund) | The loser they deliberately sold | −$55,000 |
| Net capital result | Loss exceeds gains | −$15,000 |
| → Gains cancelled | The $40,000 of gains is wiped to zero | $0 taxed |
| → Against ordinary income | The annual $3,000 maximum | −$3,000 |
| → Carried forward to 2027+ | Banked, keeps long-term character | $12,000 |
Read the payoff in dollars, because it's large. Those $40,000 of gains weren't going to be taxed at just 15% — Priya and Raj's income is over the $250,000 threshold where the 3.8% Net Investment Income Tax kicks in, so each dollar of long-term gain really faced about 15% + 3.8% = 18.8%. Wiping out the $40,000 of gains therefore saves them 18.8% × $40,000 = $7,520. Then the $3,000 that comes off their ordinary income saves tax at their 24% marginal rate — another $720. So this single harvest cuts their 2026 federal tax by about $8,240, and it *also* banks $12,000 of losses to cut future years' taxes. They spent nothing to get it; they simply sold a position that was already down.
Priya and Raj's loss harvest, married filing jointly. They had $40,000 of realized long-term capital gains from rebalancing and harvested a $55,000 long-term loss, for a net capital result of negative $15,000. The loss first cancels the $40,000 of gains, so none is taxed; then $3,000 comes off their ordinary income, the annual maximum; and the remaining $12,000 carries forward to 2027 and beyond, keeping its long-term character. The tax saved: the $40,000 of gains would have been taxed at 15% plus the 3.8% Net Investment Income Tax, or 18.8%, so erasing them saves $7,520; the $3,000 against ordinary income saves 24%, or $720; together about $8,240 this year, plus $12,000 of losses banked for future years.
One nuance worth naming so the NIIT saving isn't a black box: the 3.8% tax is charged on the smaller of your net investment income or the amount your income sits above the threshold. Because harvesting a loss *reduces your net investment income* — gains only count "to the extent they aren't offset by losses" — it shrinks that 3.8% base right alongside the ordinary tax. For a higher earner, that's the quiet bonus: every harvested dollar of loss is working against two taxes at once. (We'll meet the NIIT in full in its own lesson; here it's just the reason Priya and Raj's harvest is worth 18.8% a dollar, not 15%.)
Harvesting only feels like a sacrifice if you picture sitting in cash afterward, exposed to missing a rebound. You don't. The moment Priya and Raj sell the losing sector fund, they buy a similar-but-not-identical fund — a broad market fund instead of that one sector, say — so their money is right back in the market, tracking the same kind of recovery, while the $55,000 loss counts on their return. After 31 days they can even switch back if they want. The loss is real and booked; the market exposure never left. The only rule they must respect while doing this is the wash-sale rule — which is next.
The Rule That Guards the Loss: Wash Sales
Here's the fear that keeps people from harvesting losses at all: "What if I sell for the loss, buy back in, and it turns out I broke a rule and ruined everything?" That rule is the wash-sale rule, and it's worth learning precisely, because once you know exactly where the tripwire is, you can walk right up to it and harvest with total confidence. The rule is narrow and mechanical — it is not a trap that springs on the unwary; it's a clearly drawn line.
The rule, from IRS Publication 550 and the statute behind it (Internal Revenue Code §1091): if you sell a stock or security at a loss, and within 30 days before or 30 days after that sale you buy a substantially identical stock or security, the loss is disallowed for now — the IRS calls it a wash sale. Count the window carefully: 30 days before the sale, the sale day itself, and 30 days after is a 61-day window in total. Buy the same thing back inside that window and you can't claim the loss on this year's return. Note the two words that do all the work: it only applies to a loss (gains are free), and only to a substantially identical replacement.
The wash-sale window on a timeline. If you sell a stock or security at a loss, then buying a substantially identical security within 30 days before the sale, on the sale day, or within 30 days after — a 61-day danger zone in total — disallows the loss for this year. Two outcomes follow. In a normal taxable account the disallowed loss is not lost: it is added to the basis of the replacement shares and the old holding period carries over, so it comes back when you eventually sell — it is deferred, not destroyed. But if the replacement is bought inside an IRA or Roth IRA, the loss is disallowed and permanently gone, because an IRA has no basis to add it to (Revenue Ruling 2008-5). The safe move is to buy a not-substantially-identical replacement immediately, staying invested, and wait past day 31 before returning to the original security.
Now the reassurance that changes how the whole thing feels — and it's the single most important thing to know if you're afraid of getting this wrong. A disallowed loss in a normal taxable account is not lost. It is deferred. When a wash sale disallows your loss, the tax code doesn't burn it; it adds the disallowed loss to the basis of the replacement shares and lets the old holding period carry over. Picture Raj selling 100 shares for a $4,000 loss (he paid $10,000, sold for $6,000), then buying 100 shares back just 10 days later for $6,000. Wash sale: the $4,000 loss is disallowed *this year*. But that $4,000 is added to his new shares' basis, so instead of a $6,000 basis he has a $10,000 basis — meaning when he eventually sells for, say, $11,000, his gain is only $1,000, not $5,000. The $4,000 came back to him. He didn't lose the deduction; he just has to wait for it. A wash sale in a taxable account is a timing annoyance, not a catastrophe.
There is exactly one version of the wash sale that is genuinely unforgiving, and everyone should know it. If the replacement shares are bought inside your IRA or Roth IRA — including by an automatic reinvestment you forgot was running — the loss is disallowed AND it is gone forever. The IRS ruled on this directly (Revenue Ruling 2008-5): because an IRA has no cost basis for the tax code to step up, there is nowhere to add the disallowed loss, so unlike a taxable-account wash sale, it can never come back. Selling at a loss in your brokerage account while your IRA quietly buys the same fund is the costliest wash-sale mistake there is. Turn off auto-invest in your IRA around any harvest.
The four quiet ways people blow it
Almost nobody trips the wash-sale rule by obviously rebuying the same stock the next day — they know better. They trip it in the corners, where a purchase they didn't think of as a purchase lands inside the 61-day window. Here are the four:
- A repurchase in your IRA or Roth IRA. As above — this is the worst one, because the loss is permanently forfeited, not merely deferred. The IRS explicitly counts an IRA purchase of substantially identical shares as your purchase.
- A spouse's account. The rule reaches across a married couple: if you sell at a loss and your spouse (or a company you control) buys the substantially identical security inside the window, it's still a wash sale. The IRS treats the household as one for this. Coordinate harvests with your spouse's accounts, not just your own.
- An auto-reinvested dividend (a DRIP). This is the sneakiest. If a fund or stock you're harvesting pays a dividend that's set to automatically reinvest, that reinvestment is a *purchase* of the same security — and if it lands within 30 days of your loss sale, it triggers a (usually partial) wash sale on the reinvested shares. A tiny automatic buy can taint part of a large harvested loss. Switch dividends to cash around a harvest.
- A rebuy in the same account inside 30 days. The plain-vanilla version: you sell for the loss, then get nervous and buy the same fund back three weeks later. Wash sale. The fix is either to wait past day 31 or — far better — to buy a *different, not-substantially-identical* fund immediately so you're never out of the market.
That leaves the one genuinely gray area: what counts as substantially identical? Publication 550 is clear on the easy cases — the stocks of two *different* companies are "not ordinarily" substantially identical, so selling one company's shares at a loss and buying a competitor's is fine, and (the reason "stay invested" works) selling one fund and buying a *different* fund is generally fine. The unsettled case is two index funds that track the *same* index — say two different sponsors' S&P 500 funds. The IRS has never ruled on it, so cautious investors treat same-index funds as risky and reach for a fund tracking a *different* index (a total-market fund instead of an S&P 500 fund) to be safely clear. When in doubt, make the replacement genuinely different, not a near-clone.
Choosing Which Shares You Sell: Specific-Identification Lots
Both harvests share a hidden lever most people never touch, and it can swing your taxable result by thousands of dollars on the *very same sale*. When you've bought the same investment more than once — a bit each month, or in a few lump sums — you own several lots, each with its own purchase date and its own basis. When you sell only part of your position, *which lot you're deemed to sell* decides the gain or loss you report. And you usually get to choose, if you speak up in time. That choice is called specific identification.
The default, if you say nothing, is FIFO — first in, first out — so the broker sells your *oldest* shares first. Those are often your lowest-basis, biggest-gain shares, which is frequently the worst possible choice at tax time. The alternative is to specifically identify the lot you want sold: you tell your broker, at or before the sale, exactly which shares to sell (by purchase date and price), and the broker confirms it in writing. (A separate method, average cost, pools your basis and is available for mutual-fund and dividend-reinvestment shares — convenient, but it gives up this control.) Specific identification is how you sell the high-basis lot to *shrink* a gain, or the deepest-underwater lot to *harvest the biggest loss*.
Watch the size of the swing with Priya's fund. She built a position in three lots, and the shares are now worth $90 each:
| Lot | Bought | Basis (100 sh) | Value now | If she sells this lot |
|---|---|---|---|---|
| Lot A | 2019 @ $40 | $4,000 | $9,000 | +$5,000 long-term gain |
| Lot B | 2021 @ $120 | $12,000 | $9,000 | −$3,000 long-term loss |
| Lot C | 2022 @ $150 | $15,000 | $9,000 | −$6,000 long-term loss |
Priya owns three lots of the same fund, each 100 shares now worth $9,000. Lot A, bought in 2019 at $40 a share for a $4,000 basis, carries a $5,000 gain. Lot B, bought in 2021 at $120 for a $12,000 basis, carries a $3,000 loss. Lot C, bought in 2022 at $150 for a $15,000 basis, carries a $6,000 loss. If she sells 100 shares and says nothing, the FIFO default sells the oldest lot, Lot A, producing a $5,000 taxable gain. If she specifically identifies Lot C instead, the identical sale produces a $6,000 harvestable loss. That is an $11,000 difference in taxable result on the same sale, decided entirely by which lot she chooses — which is why you tell the broker before you sell.
If Priya needs to sell 100 shares and says nothing, FIFO hands her Lot A and a $5,000 taxable gain — the opposite of what she wants. If instead she specifically identifies Lot C, the same 100-share sale produces a $6,000 harvestable loss. That's an $11,000 difference in her taxable result, from nothing but choosing the lot — the single highest-leverage habit in this entire lesson. The rule to carry: when you sell part of a holding, never let the default choose for you. Identify the lot that serves your plan — the high-basis lot to avoid a gain, the low-basis lot to fill a 0% harvest, the deepest-loss lot to harvest.
Nudging Past the One-Year Line: Holding-Period Management
One more lever, and it's about *when* you sell, not what. The gap between short-term and long-term treatment is enormous: a short-term gain (held one year or less) is taxed at your ordinary income rate — as high as 37% — while a long-term gain (held more than a year) gets the gentle 0/15/20% rates. Sometimes you're sitting on a winner you've held for eleven months, and simply *waiting a few more weeks* to cross the one-year line converts the whole gain from ordinary rates to long-term rates. That's holding-period management.
Two details make it precise. First, the clock starts the day after you bought — so "more than one year" means you need one year plus one day; selling on the exact anniversary is still short-term. Second, the saving can be big. Suppose Priya holds a stock with a $10,000 gain and has owned it for eleven months. Sell now and it's short-term, taxed at her 24% ordinary rate plus the 3.8% NIIT — about 27.8%, or $2,780. Wait 32 more days to cross into long-term, and the same gain is taxed at 15% plus 3.8% — 18.8%, or $1,880. Those 32 days of patience are worth $900.
A timeline showing the one-year holding-period line for a $10,000 gain. Sold at 11 months the gain is short-term, taxed at Priya's ordinary 24% rate plus the 3.8% Net Investment Income Tax — 27.8% in all, or $2,780. Held just past one year and one day the same gain is long-term, taxed at 15% plus 3.8% — 18.8%, or $1,880. Waiting 32 more days to cross the line saves $900. The holding period is counted from the day after purchase, so reaching long-term takes one year plus one day; selling on the exact anniversary is still short-term.
Holding-period management is a genuine lever, but it's a judgment call, not an automatic win: waiting 32 days to save $900 also means 32 more days exposed to the stock moving against you. If it drops more than the tax saving during the wait, patience cost you money. The rule of thumb: for a position you'd be comfortable holding anyway, nudging past the one-year line is close to free money; for one you're desperate to exit, don't let a tax tail wag the investment dog. And the flip side is true for losses — a loss held just under a year is short-term, which can be more valuable because it offsets highly-taxed short-term gains first.
Crypto's Open Door: No Wash-Sale Rule (Yet)
Chad Molina trades cryptocurrency alongside his software-QA job in Denver, and his world has a quirk that stops harvesters in their tracks when they first hear it: the wash-sale rule does not apply to crypto. Not "applies loosely" — it genuinely doesn't reach it, for tax year 2026. The reason is a technicality in the statute. The wash-sale rule (§1091) is written to cover "stock or securities." The IRS has classified cryptocurrency as property, not a security (going back to Notice 2014-21). Property isn't "stock or securities," so the rule simply doesn't apply. Chad can sell Bitcoin at a loss, harvest that loss in full, and buy it back the same minute — no 61-day window, no waiting, no substantially-identical worry.
That makes crypto loss-harvesting unusually clean: in a volatile down week, a crypto investor can realize losses to offset gains (and $3,000 of ordinary income, and carry the rest forward) without ever giving up their position or their upside. It's the one corner where you get the loss *and* stay in the exact same asset with no gap.
This open door is a live target for Congress. Proposals to extend the wash-sale rule to digital assets have been introduced repeatedly — a standalone Senate bill and a bipartisan draft were both circulating in 2025 — and one nearly rode along on a larger 2025 law before being dropped. None has been enacted as of mid-2026, so the rule still doesn't apply for 2026. But this is exactly the kind of provision that can change year to year, so it must be re-checked every tax year. A separate caution: mechanically selling and instantly rebuying the same coin over and over could, in principle, draw an "economic substance" challenge — the loss still counts, but don't turn it into an obvious game. The full crypto tax picture — Form 1099-DA, per-wallet basis, staking — is its own lesson; here, just hold the one strategy fact and its expiration date.
Reading a Harvesting Worksheet: Form 8949 & Schedule D
All of this eventually lands on paper — on Form 8949 (where each sale is listed line by line) and Schedule D (where those lines are totaled and netted). You don't need to fill these out by hand; software and your broker's records do most of it. But you should be able to *read* the harvesting story on them, because that's how you confirm your harvest worked, how you'd catch a broker's wash-sale adjustment, and how you'd track a carryover to next year. Let's read a sample built from Priya and Raj's harvest, with the specific-ID lots, the wash-sale code, and the carryover line all visible.
A sample of Priya and Raj's 2026 Form 8949, Part II (long-term), and Schedule D, shown whole. Form 8949 lists three long-term sales. First, a specifically-identified losing sector fund: $30,000 proceeds, $85,000 cost basis, a $55,000 loss. Second, rebalancing winners: $140,000 proceeds, $100,000 basis, a $40,000 gain. Third, a small tech ETF where an automatic dividend reinvestment triggered a wash sale: $9,000 proceeds, $10,000 basis — a $1,000 raw loss that is disallowed, so it carries code W in column (f) and a positive $1,000 adjustment in column (g), netting to $0. The long-term totals are $179,000 proceeds, $195,000 basis, a $1,000 adjustment, and a net $15,000 loss. Schedule D carries that to line 15 (long-term) and line 16 (combined) as negative $15,000. Line 21 sends the smaller of the loss or $3,000 — so $3,000 — to Schedule 1 to reduce ordinary income, and the Capital Loss Carryover Worksheet rolls $12,000 forward to 2027 as a long-term loss. The lines the lesson reads are highlighted.
Walk it top to bottom, the way you'd check your own. Form 8949, Part II (long-term) lists each sale: the description, the dates acquired and sold, the proceeds, and the cost basis — and because Priya used specific identification, the basis shown is the exact lot she chose, not FIFO's. Any sale caught by a wash sale gets a code "W" in column (f) and the disallowed loss entered as a positive adjustment in column (g), which mechanically adds it back so it isn't deducted this year — that column is where a wash sale becomes visible on the return. Schedule D then carries the Form 8949 totals into Part II (long-term), combines them with any short-term results from Part I, and reaches the net figure on line 16 — here a −$15,000 loss. From there two things happen: line 21 sends the allowed $3,000 over to Schedule 1 and the 1040 to reduce ordinary income, and the Capital Loss Carryover Worksheet computes the $12,000 that rolls to 2027, keeping its long-term character on next year's Schedule D. Every number we computed by hand is sitting on these two forms — which is exactly how you'd verify a harvest really happened.
You almost never build these forms from scratch — your broker issues a Form 1099-B (and, for crypto, the new 1099-DA) that feeds most of it, and tax software fills 8949 and Schedule D from there. Your job is to (1) tell the broker which lots to sell before you sell them, (2) glance at the 1099-B's realized gain/loss and wash-sale columns to confirm the harvest came through, and (3) note any carryover so you don't forget to use it next year. Reading the forms is a five-minute check, not an afternoon of arithmetic.
Audit & Scam Watch: Where Harvesting Goes Wrong
Harvesting is legitimate, but it lives next door to a few real dangers — some are honest mistakes the IRS will catch, and some are pitches designed to fool you. You don't need to memorize them; you need the tells and one protective rule.
Scam and Audit Watch for harvesting. First trap: the accidental wash sale — claiming a loss on a security you, your IRA, or your spouse rebought within 30 days, or that an auto-reinvested dividend rebought; brokers report wash sales on Form 1099-B and the IRS matches them, so it surfaces as a notice. Prevent it by pausing IRA auto-invest and setting dividends to cash around a harvest. Second: tax-loss harvesting services that over-promise, hiding that the benefit is mostly deferral, is worthless in a tax-advantaged account, and can trigger wash sales through aggressive rebuying. Third: outright fake losses and inflated cost basis sold as clever strategies, where the filer who signs is liable. The one rule: a loss is only real if you don't repurchase a substantially identical security within 30 days anywhere you control, and a gain or loss is only real if the sale and its basis are real and documented. Report an abusive promoter with Form 14242, a bad preparer with Form 14157, and suspected fraud with Form 3949-A; fix your own return by amending with Form 1040-X.
The most common harvesting problem isn't fraud — it's a wash sale you didn't mean to create, most often from a repurchase in another account (an IRA, a spouse's account) or an auto-reinvested dividend. Brokers report your sales and wash-sale adjustments to the IRS on Form 1099-B, and the IRS's computers match them against your return, so a disallowed loss you claimed anyway tends to surface as a notice. It's usually not an audit — it's a correction. The tell is claiming a loss on a security you (or your IRA, or your spouse) bought within 30 days. The fix is prevention: one security, one account view, dividends set to cash, IRA auto-invest paused, around any harvest.
Some robo-advisors and newsletters sell "automated tax-loss harvesting" as a guaranteed money-maker. Done well it's a real, modest benefit — but watch for over-promising: pitches that quote a fixed "you'll save X%" with no mention that the benefit is mostly a deferral (you're lowering today's tax by lowering your basis, which raises a future gain), that it's worthless in a tax-advantaged account, or that aggressive automated rebuying can itself brush against wash-sale and same-index questions. A harvest defers and rearranges tax; it rarely erases it. If a service implies free money with no trade-off, it's overselling.
The outright-fraud version: schemes that manufacture a loss that never happened, or that inflate your cost basis to shrink a gain — sometimes dressed up as sophisticated "tax strategies," straddles, or offsetting-position trades sold by a promoter for a fee. Reporting a loss on a sale that wasn't economically real, or a basis you can't document, is not harvesting; it's a false return, and it's the filer who signs it who is liable. If a "strategy" produces a paper loss with no real economic loss behind it, or a basis number you can't trace to what you actually paid, walk away.
A loss is only real if you don't repurchase a substantially identical security within 30 days — anywhere you control, including your IRA, your spouse's account, and automatic reinvestments. And a gain or loss is only real if the sale and its basis are real and documented. Get those two right and no harvesting trap — accidental or predatory — can reach you.
WHERE: a promoter selling a fake-loss or basis-inflation "strategy" → report to the IRS with Form 14242 (abusive tax scheme) or the Whistleblower Office; a preparer who put a bogus loss on your return → Form 14157; suspected tax fraud generally → Form 3949-A. If you realize your OWN return has a wash-sale or harvest error, you fix it by amending (Form 1040-X), not by reporting yourself. WHAT TO HAVE READY: your 1099-B and 1099-DA, your own record of purchase dates and prices (basis), the tax years involved, and any promotional material or preparer paperwork. WHY: reporting an abusive promoter isn't turning someone in for a technicality — these schemes leave the taxpayer holding the liability, and flagging one protects the next person who's shown the same too-good-to-be-true pitch.
If This Already Happened to You
Maybe this lesson landed with a small jolt of recognition — you sold something at a loss last year and bought it right back, or your IRA was quietly auto-investing while you harvested in your brokerage account, or you just filed and now you're not sure the loss you claimed was allowed. Take a breath. The rules here are genuinely intricate — the wash-sale rule catches full-time investors and even tax pros — and getting one wrong doesn't mean you cheated or that you're in trouble. It means you did something the system never explained, and almost all of it is fixable.
The most important reassurance is the one from the wash-sale section, and it bears repeating because it's the exact thing people panic about: in a normal taxable account, a disallowed loss is not lost — it's added to your replacement shares' basis, so it comes back to you when you eventually sell. You didn't set fire to the deduction; you deferred it. Here's what to do depending on what happened:
- You triggered a wash sale in your brokerage account. Usually nothing dramatic is required — your broker likely already applied the adjustment on your 1099-B, adding the disallowed loss to your new shares' basis. If you claimed the loss anyway and it should have been disallowed, file an amended return (Form 1040-X) to correct it; the loss isn't gone, it's just deferred into your basis.
- The repurchase was in your IRA. This is the hard one — that loss is permanently disallowed. There's no way to recover it, but there's a lesson to bank: pause IRA auto-invest around future harvests. Going forward you'll never repeat it, and one lost loss is a tuition payment, not a disaster.
- A wash sale came from an auto-reinvested dividend. Often only a small slice of your loss is affected (just the reinvested shares). Amend if you claimed the full loss, and switch that holding's dividends to cash before your next harvest.
- A notice arrived (a CP2000) because a claimed loss was disallowed. This is a computer match, not an audit — it proposes a change and gives you a specific window to agree or explain. Often the fix is simply agreeing and paying a small difference, or showing that the basis adjustment already handled it. Opening it is far less painful than the imagined version.
And if you *missed* a harvest you could have made — a 0% gain-harvest year that came and went, a loss you never booked — that's not a mistake to grieve, just a strategy to remember next time. Losses you already have carry forward indefinitely, waiting for you. The worst outcome in this whole area isn't a wash sale; it's never learning the moves at all. You're past that now.
Where to Get Help — the Harvesting Recourse Stack
Harvesting help has a natural ladder, and the good news is that the first two rungs are free and probably already yours. Most people never need a paid professional for a straightforward harvest; the records you need are sitting in your brokerage account. Here's the stack, most accessible first.
- Your broker's realized gain/loss and wash-sale reports — start here. Every major brokerage gives you a running realized gain/loss report, a cost-basis view with your lots, a lot-selection tool for specific identification, and a wash-sale column that flags disallowed losses automatically. This is your primary instrument: it tells you your 0% room won't be blown, which lots to sell, and whether a wash sale is brewing. Learn where these live in your account before you harvest.
- IRS Publication 550 and the Schedule D / Form 8949 instructions — the free, authoritative source. Pub 550 ("Investment Income and Expenses") is the plain-language rulebook for wash sales, basis, holding periods, and the loss limit; the Schedule D and 8949 instructions walk the mechanics. It's free at IRS.gov and it's what the pros are reading too.
- A CPA or enrolled agent for a large or complex portfolio. When you're coordinating harvests across many accounts, holding concentrated or illiquid positions, dealing with equity compensation, or your harvest interacts with the AMT, NIIT, or a business, a professional who does this earns their fee — this is one of the clearer cases where paid advice pays for itself. Look for someone who'll model the harvest, not just record it after the fact.
- The Taxpayer Advocate Service (TAS) if a harvest error becomes an IRS dispute you can't resolve. If a disallowed-loss notice spirals, or you're facing a hardship while trying to fix a return, TAS is the free, independent IRS office that helps when normal channels stall. It's the backstop, not the first stop — but it's there.
Two things to keep in mind. First, your broker's wash-sale reporting only sees the accounts at that broker — it cannot know your IRA at a different firm, your spouse's account, or your DRIP at another fund, which is exactly where the cross-account wash sales hide; you have to connect those dots yourself. Second, IRS phone help is thin and seasonal, and the folks answering can't give investment advice — so for anything beyond reading a notice, the written sources (Pub 550) and a professional are more reliable than the phone line. Match the question to the right rung and you'll spend far less time on hold.
The Questions Almost Everyone Asks
The same handful of harvesting questions come up again and again. Quick, plain answers, each pointing back to where the fuller story lives in this lesson.
- Can I really pay 0% tax on an investment gain? Yes — if your total taxable income (after your deduction) plus the gain stays under the 0% breakpoint ($49,450 single, $98,900 married filing jointly for 2026). Your ordinary income fills the space first; the gain that still fits below the breakpoint is taxed at 0%. It's a permanent bracket, aimed at modest incomes.
- I sold at a loss and rebought — did I ruin it? Probably not, and even if it's a wash sale, in a taxable account the disallowed loss is added to your new shares' basis and comes back when you sell. The only version that's permanently lost is a repurchase inside an IRA. Rebuying a *different* (not substantially identical) security is always fine.
- How long do I have to wait to buy back in? For a loss, avoid buying the substantially identical security for the full 61-day window (30 days before through 30 days after). But you don't have to sit in cash — buy a similar-but-different fund immediately and you're invested the whole time. For a gain, there's no waiting period at all; buy it right back.
- Which shares should I sell? Whichever lot serves your goal — use specific identification, not the FIFO default. Sell the highest-basis (smallest-gain or biggest-loss) lot to harvest a loss or avoid a gain; sell a low-basis lot to fill a 0% gain-harvest year. Tell your broker before the sale.
- Does harvesting a loss help my regular paycheck income? A little, directly: after losses cancel your capital gains, up to $3,000 of leftover loss comes off your ordinary income each year, and the rest carries forward. So yes, but it's capped at $3,000 a year against wages.
- Do capital losses ever expire? No. Unused losses carry forward indefinitely, keeping their short- or long-term character, until you use them up. (Individuals can't carry them *back* to past years, only forward.)
- Is a big refund from harvesting free money? No — much of a loss harvest's value is deferral, not elimination: booking a loss today often lowers your basis or offsets a gain you'd have paid later anyway. It's real and worth doing, especially for higher earners facing the extra 3.8% NIIT, but treat it as smoothing and shifting tax, not erasing it.
- My income is too high for the 0% bracket — is gain harvesting useless for me? For the 0% move, yes — if your ordinary income already exceeds the breakpoint, there's no 0% room. But loss harvesting is *more* valuable the higher your income, because your gains (and the 3.8% NIIT) are taxed harder, so each harvested loss saves more.
- Crypto — same rules? Not for the wash-sale rule: crypto is treated as property, so for 2026 there's no wash-sale restriction — you can sell a coin at a loss and rebuy instantly. That could change if Congress acts, so re-check each year; the full crypto picture is its own lesson.
- Should I harvest just because the market dropped? Only if it fits your plan. Harvesting a loss is worth doing when you have gains to offset or income to reduce and you can stay invested through a replacement — but don't sell a good long-term holding purely to book a loss if it complicates your portfolio or risks a wash sale. The tax tail shouldn't wag the investment dog.
Check Yourself: Model Your Own Harvest
You've seen both moves worked out — Nadia's 0% gain harvest and Priya and Raj's loss harvest. Now run your own numbers. The modeler below lets you pick either harvest. For a gain harvest, enter your filing status, your ordinary taxable income, and a gain you're thinking of realizing; it shows your 0% room and how much of the gain lands at 0% versus 15%. For a loss harvest, enter your realized gains and the loss you'd book; it shows what cancels, the $3,000 that comes off ordinary income, your carryover, and a rough tax saved — with a wash-sale reminder built in. It's pre-filled with Nadia's and Priya & Raj's exact figures so you can confirm the lesson's math, then clear it for your own.
An interactive harvesting modeler with two modes. In gain-harvest mode you enter your filing status, your ordinary taxable income, and a long-term gain you are thinking of realizing; it computes your 2026 zero-percent room — the 0% breakpoint (Single $49,450, Married filing jointly $98,900) minus your ordinary income — then how much of the gain is taxed at 0% versus 15%, and the tax on the gain. It is pre-filled with Nadia: single, $41,180 of ordinary income, an $8,270 gain, giving $8,270 of room, the whole gain at 0%, and $0 tax. In loss-harvest mode you enter your realized gains and the loss you would harvest; it nets them, applies the $3,000 annual ordinary-income limit, shows the carryover, and estimates the tax saved assuming a higher earner (18.8% on cancelled gains, 24% on the $3,000). It is pre-filled with Priya and Raj: $40,000 of gains and a $55,000 loss, giving $40,000 cancelled, $3,000 off ordinary income, $12,000 carried forward, and about $8,240 saved. A wash-sale reminder is always shown. Nothing you enter is saved.
As you experiment, watch two things. In gain mode, raise your ordinary income and watch the 0% room shrink to nothing — that's why a low-income year is the opportunity. In loss mode, notice how the first dollars of loss are worth the most (they cancel gains taxed at 15% or 18.8%), while everything past your gains plus $3,000 just becomes a carryover — valuable, but only next year. This is a teaching estimate that uses the 2026 federal brackets and skips state tax and the finer edges, but it makes the shape of your own harvest visible, which is the whole point.
Glossary — the Words You Now Own
Every term this lesson introduced, in one place — the vocabulary of deliberate harvesting.
- Harvesting — deliberately triggering a sale for its tax result (not because you need the money), then usually getting back into a similar position so you stay invested.
- Tax-loss harvesting — selling an investment that's down to realize a capital loss, using it to offset realized gains and up to $3,000 of ordinary income, and carrying the rest forward — while buying a not-substantially-identical replacement to stay in the market.
- Gain harvesting (basis reset) — in a low-enough-income year, deliberately realizing a long-term gain that falls in the 0% capital-gains bracket, paying $0 tax, and rebuying to step your cost basis up so a future sale is smaller.
- 0% capital-gains bracket — a permanent long-term-gains rate of 0% for taxable income up to a breakpoint ($49,450 single / $98,900 married filing jointly for 2026); the basis of gain harvesting.
- Stacking — the rule that ordinary income fills the brackets first and long-term gains sit on top, so your 0% room equals the 0% breakpoint minus your ordinary taxable income.
- Wash-sale rule (§1091) — disallows a loss if you buy a substantially identical security within 30 days before or after the loss sale (a 61-day window); the disallowed loss is added to the replacement's basis (deferred), except in an IRA, where it's permanently lost.
- Substantially identical — the wash-sale rule's test for a replacement: the same security (or same-index fund) is caught; a different company's stock or a different-index fund generally is not. The same-index-fund case is an unsettled gray area.
- Specific identification (specific-ID) — telling your broker exactly which lot of shares to sell (by date and price) at or before the sale, so you control the gain or loss — versus the FIFO default, which sells your oldest shares first.
- Lot — a batch of shares bought at one time and price, with its own basis and holding period; a holding built over time is made of several lots.
- Holding-period management — timing a sale to cross the more-than-one-year line so a gain is taxed at long-term (0/15/20%) rather than short-term (ordinary) rates; the clock starts the day after purchase.
- Capital-loss carryover — unused net capital loss above the $3,000 annual ordinary-income limit, carried forward indefinitely (keeping its short- or long-term character) to offset future gains and income.
- Net Investment Income Tax (NIIT) — an extra 3.8% tax on investment income for filers over $250,000 married filing jointly / $200,000 single (not inflation-indexed); harvesting a loss reduces the income it applies to.
Key takeaways
- Harvesting is two legal, deliberate moves — not a loophole and not only for the wealthy: harvest a loss to cut this year's tax, or harvest a gain in the 0% bracket to reset your basis at no cost.
- There is a real 0% long-term capital-gains rate for 2026 — for taxable income up to $49,450 (single) or $98,900 (married filing jointly) — and because gains stack on top of ordinary income, your 0% room is the breakpoint minus your ordinary taxable income. Even Nadia, on $58,000, has $8,270 of room to realize gains at $0 federal tax.
- A harvested loss nets against gains of the same type first, then across types; up to $3,000 of leftover loss comes off ordinary income each year, and the rest carries forward forever. For higher earners the saving is bigger because gains also face the 3.8% NIIT — about 18.8% a dollar, not 15%.
- The wash-sale rule disallows a loss only if you buy a substantially identical security within the 61-day window (30 days before or after). Stay invested by buying a not-substantially-identical replacement — that's the move that keeps you in the market while the loss counts.
- A wash-sale loss in a normal taxable account isn't lost — it's added to your replacement shares' basis and comes back when you sell. The one exception is a repurchase in an IRA, where the loss is gone forever (Rev. Rul. 2008-5). Watch spouse accounts and auto-reinvested dividends too.
- Use specific identification to choose which lot you sell — the difference between FIFO's oldest, biggest-gain shares and a hand-picked losing lot can be an $11,000 swing on the same sale. And nudge a winner past the one-year line to turn short-term ordinary rates into long-term 15%.
- Gain harvesting only works with an appreciated long-term holding in a taxable account, and a 0%-taxed gain still raises your AGI — which can touch ACA subsidies, IRMAA, Social Security taxation, and phase-outs — so land it inside the room and check the side effects.
- Crypto has no wash-sale rule for 2026 (it's property, not a security), so a crypto loss can be harvested and the coin rebought instantly — but that could change if Congress acts, so re-verify every tax year.
Knowledge check
8 questions
Nadia is single with $41,180 of ordinary taxable income for 2026, when the single 0% long-term capital-gains breakpoint is $49,450. How much long-term gain can she realize and pay $0 federal tax on?