Learn

A field guide for serious investors.

Plain explanations of tax-loss harvesting, direct indexing, fee math, and the engine that runs HarvestEngine. Built for self-directed investors and skeptical professionals who want clear reasoning, not hand-wavy marketing.

Start with TLH 101 See the algorithm

The math

Tax alpha, fee shape, and the structural differences that change after-tax outcomes.

9 articles

2026-04-26 · 8 min · basics· comparison

TLH vs ETF rebalancing: which actually saves you money?

One ETF gives you one place to harvest. A direct-index sleeve gives you many. That structural difference is the simplest honest reason direct indexing exists.
2026-04-26 · 8 min · fees· math

Why subscriptions beat percentage-of-assets fees at $250K and up

The shape of the fee matters more than most investors realize. A subscription stays fixed. A percentage-of-assets fee scales with your wealth forever.
2026-04-26 · 8 min · taxes· concepts

Tax alpha: the return your portfolio earns by paying less tax

Tax alpha is not magic and it is not stock-picking alpha. It is the after-tax improvement that comes from smarter loss harvesting, gain deferral, and lot selection.
2026-05-01 · 6 min · upsell· fees

When does the AI Designer + tax-loss math justify the $49?

The Sandbox shows you how the engine thinks. Guided is when you bring real money. Here's the threshold where the tax math actually pays the subscription back, and the threshold below which a Vanguard ETF is the better answer.
2026-05-24 · 9 min · taxes· lot-selection

FIFO, LIFO, HIFO, specific-ID: how lot selection changes your tax bill

Every time you sell shares from a multi-lot position, the IRS allows you to designate which lots are being sold. That choice — FIFO, LIFO, HIFO, or specific-ID — determines your cost basis and can change the tax outcome significantly. Here is how each method works and why lot selection is a first-class concern in any tax-aware portfolio.
2026-06-04 · 9 min · taxes· mechanics

Capital loss carryforward: how the §1212 carry extends TLH value across years

A harvested loss does not expire if there are no gains to offset in the year it is realized. IRC §1212 allows unused capital losses to carry forward indefinitely, retaining their short-term or long-term character, and apply against future capital gains or ordinary income. Understanding the carry mechanics — the approximately $3,000 ordinary income limit, the character ordering rules, and the multi-year planning implications — changes how a systematic harvesting program should be evaluated.
2026-06-05 · 9 min · taxes· irmaa

IRMAA: how Medicare's income surcharge creates a hidden harvest argument

Medicare premiums are not flat for every beneficiary. The Income-Related Monthly Adjustment Amount steps up Part B and Part D premiums in graduated tiers for higher-income participants, using a two-year income lookback. Capital gains events can push MAGI across a tier boundary; harvested losses can pull it back — potentially reducing Medicare surcharges in addition to the regular capital gains tax and NIIT.
2026-06-06 · 9 min · taxes· etf

Why ETFs are more tax-efficient than mutual funds in taxable accounts

For investors in taxable accounts, the choice between an ETF and a mutual fund tracking the same index is not just about expense ratios or trading flexibility. The two vehicle types handle internal capital gains in structurally different ways, and that structural difference may show up as a tax bill each December even in years when the investor never sold a single share.
2026-06-03 · 9 min · taxes· niit

The 3.8% Net Investment Income Tax: how harvested losses can reduce the surcharge

For investors whose income crosses the NIIT threshold, capital gains face a second federal computation: the 3.8% Net Investment Income Tax under IRC §1411. Because the NIIT applies to net investment income, harvested losses that offset capital gains can reduce this surcharge directly — a second layer of benefit that the single-system framing misses.

The rules

Wash sales, basis tracking, and the IRS code sections that decide whether a move is actually clean.

11 articles

2026-04-26 · 10 min · compliance· advanced

The wash-sale rule, demystified

If you sell at a loss and buy back something substantially identical inside the window, the IRS can disallow the loss. This is the line between smart harvesting and self-inflicted damage.
2026-04-26 · 8 min · taxes· estate

The step-up basis: why long-horizon tax planning is more powerful than it first looks

Tax-loss harvesting is often described as a temporary deferral. Long-horizon estate rules can make that framing much too simplistic.
2026-05-21 · 9 min · compliance· wash-sales

What counts as 'substantially identical' for §1091?

The wash-sale rule turns on three words the IRS has never fully defined: substantially identical. Same-CUSIP shares are clear. Same-index ETFs are a gray area. IRA purchases can permanently destroy a loss. Here is what the revenue rulings actually say.
2026-04-26 · 9 min · taxes· compliance

The IRS code behind tax-loss harvesting: the practical cheat sheet

You do not need to memorize the whole tax code. You do need to understand the few sections that determine whether a harvest is usable, a hedge is clean, and a long-horizon plan actually works.
2026-05-22 · 9 min · taxes· state-taxes

How TLH interacts with state taxes (California, NY, others)

Tax-loss harvesting is usually framed as a federal tax strategy. But in high-tax conforming states like California and New York, every harvested loss may save at the combined federal-plus-state rate — making TLH potentially more valuable than the federal-only math suggests. Here is the state-by-state picture, including the Pennsylvania exception.
2026-05-23 · 8 min · wash-sales· dividends

Dividend washing: when a dividend turns a loss harvest into a problem

A position that falls by exactly its dividend amount has not really lost money — the market simply repriced. Harvesting that 'loss' runs into two separate IRS rules: §246's holding-period requirement can strip the dividend of its qualified rate, and §1091's wash-sale rule can disallow the capital loss. Here is how both traps work and what they mean for tax-aware investors.
2026-05-26 · 9 min · taxes· filing

Form 8949 walkthrough: how to actually file your harvested losses

Every tax-loss harvest eventually lands on IRS Form 8949 — the transaction-level schedule that feeds Schedule D. Understanding which part your harvested lots land in, what the three basis-reporting columns mean, and how wash-sale disallowances appear as code W adjustments is what separates a cleanly filed return from one that invites IRS follow-up questions.
2026-05-27 · 9 min · crypto· wash-sales

Tax-loss harvesting with crypto: the §1091 gap and what to watch

Cryptocurrency's IRS property classification places it outside IRC §1091's wash-sale rule, creating an opportunity for more aggressive loss harvesting. Multiple legislative proposals have sought to close this gap, and the rules may change. Here is the current state of the §1091 exemption, the gray areas that exist even without it applying, and what investors in a tax-aware portfolio need to know about the regulatory horizon.
2026-05-30 · 9 min · wash-sales· spouse

Wash sale rules across spouse accounts: the household pool

Most investors think of the wash-sale rule as a one-account timing problem. Revenue Ruling 2008-5 extends §1091's disallowance logic to spousal accounts and IRAs: a purchase in a spouse's account or retirement account inside the 61-day window may disallow a loss in the harvesting account. When that purchase is in an IRA, the normally-deferred basis carryover may not apply — and the tax benefit may be permanently unavailable.
2026-06-01 · 8 min · taxes· mechanics

Cost basis when you transfer between brokers: the ACAT trap

When moving a brokerage account through ACAT, the shares transfer in-kind without triggering a taxable sale. But cost basis records travel on a separate channel that may fail for older lots, multiply-transferred accounts, or positions with complex corporate-action histories. Unknown basis at the receiving broker can distort every harvest decision that follows.
2026-06-02 · 9 min · taxes· amt

Alternative Minimum Tax + harvested losses: edge cases

For most taxable investors, the Alternative Minimum Tax does not materially change how harvested losses work: capital gains and losses use the same preferential rates under both regular and AMT computations. The edge cases are narrower but important — incentive stock options create a basis divergence that can make a 'loss' under one system look like a 'gain' under the other, and states like California run their own AMT that was not restructured by TCJA.

Strategy

Loss banks, pacing, concentrated-stock planning, and advanced overlays in the real world.

10 articles

2026-04-26 · 8 min · advanced· rsu

Concentrated stock + RSUs: tax planning when one ticker dominates

Concentrated stock is not just a risk problem. It is a risk-and-tax problem at the same time. Here is how direct indexing and pacing make the unwind smarter.
2026-04-26 · 9 min · taxes· advanced

The art of pacing: why timing your harvests through the year matters

TLH is not just about seeing a loss and clicking sell. It is about building a usable loss bank, avoiding bad timing, and realizing gains intentionally when the year is right.
2026-04-26 · 8 min · taxes· strategy

The zero-tax exit: pairing losses with gains for a $0 tax bill

A harvested loss bank is not just this year's tax help. It can become a strategic reserve for future diversification, rebalancing, and liquidity decisions.
2026-04-26 · 8 min · short· risk

Using short positions as escape hatches on risky long bets

Short positions are not only about trying to profit from decline. In the right setup, they can help reshape risk around appreciated long holdings without forcing a crude sell-now decision.
2026-05-01 · 8 min · upsell· advanced

When the long sleeve isn't enough

Long-only TLH is a real win. But for high-income / RSU-heavy / concentrated-stock cases, the long side runs out of harvestable losses before the year does. The short overlay generates additional realized losses without permanently changing your market exposure. Here's the case for it, and the cases against.
2026-05-25 · 9 min · taxes· estate

The estate step-up: why holding losers can still be the right call

Tax-loss harvesting is usually presented as a clear win: realize the loss, defer the gain, keep market exposure intact. But IRC §1014's estate step-up rule can change the long-term arithmetic. For investors with a long horizon and explicit estate plans, the choice between harvesting now, holding, and donating may benefit from explicit position-level reasoning rather than a default annual-harvest approach.
2026-05-28 · 9 min · taxes· estate

Donating appreciated stock vs harvesting losses: when each wins

Donating long-term appreciated stock directly to a charity or donor-advised fund may eliminate the embedded capital gain entirely under IRC §170 — not defer it. Tax-loss harvesting addresses a different part of the portfolio: it creates realized losses to offset gains that must first be recognized. For investors with philanthropic intent, understanding which positions get which treatment can make both strategies significantly more effective.
2026-05-29 · 9 min · taxes· roth

Roth conversions + TLH: timing the year for maximum offset

Roth conversions and tax-loss harvesting address different parts of the income picture. A conversion adds ordinary income; harvested losses offset capital gains and may free up bracket space for a more efficient conversion. Here is how the two strategies interact — and the common mistakes that come from treating them independently.
2026-05-31 · 9 min · taxes· rebalancing

Should you rebalance in your 401(k) or your taxable account?

Rebalancing inside a 401(k) generates no immediate tax event. The same trade in a taxable brokerage account may recognize years of accumulated gain at the moment of sale. For investors running both account types, routing rebalancing trades toward the right venue — or turning taxable-account rebalancing into a tax-loss harvest — can make a meaningful difference over time.
2026-06-07 · 9 min · taxes· strategy

Tax-gain harvesting: realizing gains at the 0% rate to reset cost basis

Tax-loss harvesting is well documented. Its counterpart — deliberately realizing appreciated gains in years when income qualifies for the 0% federal capital gains rate — is less discussed but can be equally valuable. By recognizing a gain at potentially 0% and immediately repurchasing, the investor resets cost basis to the current price, potentially reducing the future tax cost of the same position when rates are higher. No wash-sale equivalent restricts gains.

Concepts

The portfolio-construction ideas underneath the product — beta, sleeve structure, direct-index design.

6 articles

2026-04-26 · 9 min · fit· decision

Direct indexing in 2026: who needs it, who doesn't

Direct indexing is not for everyone. But for the right taxable account, it creates a much better tax surface than a plain ETF. Here is how to decide where you actually fall.
2026-04-26 · 8 min · advanced· short

Short overlay: when extra flexibility is worth the complexity

A short overlay can add risk control and flexibility on top of a long-only tax-aware portfolio. It can also add a lot of complexity fast. Here is when it earns its place and when it clearly does not.
2026-04-26 · 7 min · concepts· risk

Beta, in plain English: why your portfolio's risk is mostly the market's risk

Beta is the market-sensitivity dial underneath the portfolio. If you do not understand it, you do not fully understand what your portfolio is likely to do in a real drawdown.
2026-04-26 · 10 min · concepts· advanced

The three sleeves: beta, long, and short — and why the structure matters

A serious tax-aware portfolio is easier to understand when you separate clean beta exposure from the long tax-aware sleeve and the optional short overlay.
2026-05-01 · 7 min · upsell· autonomy

From hand-approve to lights-out — what changes in Autopilot?

Guided makes you press Approve on every trade. Autopilot lets the engine close the loop within rails you set — daily caps, veto window, kill switch. Here's how the autonomy graduation works and when it earns its $99/month.
2026-05-07 · 10 min · margin· concepts

Margin, demystified: cash, SMA, and why your buying power is bigger than your cash

Open a margin account and your broker hands you four different 'cash' numbers — Investable Cash, Net Cash, Adjusted SMA, Margin Buying Power — and they can differ by 40×. Here's what each one means, when it matters, and why HarvestEngine only shows margin metrics on accounts you've explicitly designated for the short overlay.