How LLC Owners Save on Taxes in 2026

TLH Examples: 7 Tax-Loss Harvesting Strategies for 2026

TLH Examples: 7 Tax-Loss Harvesting Strategies for 2026

For the 2026 tax year, TLH examples demonstrate how high-net-worth investors strategically sell underperforming assets to offset capital gains and reduce taxable income. With the Tax Cuts and Jobs Act brackets maintained and new OBBBA provisions in effect, sophisticated tax-loss harvesting delivers substantial savings for wealthy investors managing complex portfolios across multiple asset classes and currencies.

Table of Contents

Key Takeaways

  • For 2026, TLH examples offset up to $3,000 ordinary income annually, with unlimited carryforward
  • The 30-day wash sale rule prohibits repurchasing substantially identical securities before or after sales
  • High-net-worth investors combine TLH with the 3.8% NIIT to maximize tax reduction strategies
  • Multi-currency portfolios require FX-aware lot selection for accurate reporting under 2026 regulations
  • OBBBA’s permanent $15 million estate exemption creates new wealth transfer opportunities with coordinated TLH

What Is Tax-Loss Harvesting and How Does It Work in 2026?

Quick Answer: Tax-loss harvesting is the practice of selling investments at a loss to offset capital gains. For 2026, losses offset gains dollar-for-dollar, reducing your tax liability under current IRS Publication 550 guidance.

Tax-loss harvesting remains one of the most powerful strategies for high-net-worth investors in 2026. The technique involves strategically realizing losses from underperforming investments to offset taxable capital gains. When properly executed, TLH examples demonstrate significant tax savings while maintaining portfolio diversification and investment objectives.

Under current tax law, capital losses offset capital gains on a dollar-for-dollar basis. Any excess losses beyond your gains can offset up to $3,000 of ordinary income annually. Remaining losses carry forward indefinitely to future tax years, creating a valuable tax asset for long-term planning.

How the 2026 Capital Gains Tax Structure Affects TLH

For the 2026 tax year, long-term capital gains continue to be taxed at preferential rates of 0%, 15%, or 20%. However, high-income investors face an additional 3.8% Net Investment Income Tax (NIIT) on investment income when modified adjusted gross income exceeds $200,000 for married filing jointly or $140,000 for single filers. This brings the effective top rate to 23.8% for long-term gains.

Consequently, TLH examples in 2026 deliver maximum value for investors in the highest brackets. A $100,000 harvested loss offsetting long-term gains saves $23,800 in federal taxes alone. When combined with state taxes in high-tax jurisdictions, total savings can exceed $30,000.

Basic TLH Mechanics: A Simple Example

Consider an investor who purchased 1,000 shares of a technology stock at $150 per share in 2024. By October 2026, the position has declined to $110 per share, creating an unrealized loss of $40,000. The investor also holds winning positions with $40,000 in unrealized gains.

Without TLH, selling the winning position triggers $40,000 in taxable gains. At the top 23.8% rate, this creates a $9,520 tax liability. However, by harvesting the $40,000 loss first and then selling the gain position, the investor eliminates the entire tax bill. The investor can immediately reinvest in a similar but not substantially identical security to maintain market exposure.

Pro Tip: Document your TLH transactions thoroughly for IRS Form 8949 reporting. Maintain records showing purchase dates, sale dates, and the 30-day wash sale compliance window.

Long-Term vs. Short-Term Losses: Strategic Considerations

The IRS requires taxpayers to match long-term losses against long-term gains and short-term losses against short-term gains first. Any remaining losses then offset the opposite type of gain. This creates strategic opportunities in TLH planning.

Short-term capital gains face taxation at ordinary income rates up to 37% in 2026, significantly higher than the 20% maximum for long-term gains. Therefore, harvesting short-term losses to offset short-term gains delivers greater tax savings. Advanced TLH examples prioritize identifying which loss type provides maximum benefit based on your specific gain composition.

What Are the Wash Sale Rules for TLH in 2026?

Quick Answer: The wash sale rule disallows loss deductions when you purchase substantially identical securities within 30 days before or after the sale. For 2026, strict compliance is essential to preserve TLH benefits.

The wash sale rule represents the primary constraint on tax-loss harvesting strategies. Under IRC Section 1091, if you sell a security at a loss and purchase a substantially identical security within 30 days before or after the sale, the IRS disallows the loss deduction. The disallowed loss instead adds to the cost basis of the replacement security.

This 61-day window (30 days before plus the sale date plus 30 days after) requires careful planning in all TLH examples. Many investors unknowingly trigger wash sales through automated dividend reinvestment programs, spousal accounts purchasing the same security, or substantially identical holdings in retirement accounts.

What Qualifies as “Substantially Identical”?

The IRS has not provided a precise definition of “substantially identical,” creating interpretive challenges. However, established guidance and case law provide clear boundaries for safe TLH practices:

  • Clearly substantially identical: Same stock in same company, same bond with identical terms
  • Generally substantially identical: Stock and call options on same stock, bonds from same issuer with similar maturity
  • Generally not substantially identical: Different companies in same industry, different ETFs tracking same index
  • Safe harbors: Switching from individual stock to broad sector ETF, replacing one S&P 500 ETF with another

The most common TLH examples involve selling an ETF and immediately purchasing a different ETF tracking a similar but not identical index. For instance, selling the Vanguard S&P 500 ETF (VOO) and purchasing the Schwab S&P 500 ETF (SWPPX) clearly avoids wash sale concerns, as they are issued by different companies despite tracking the same index.

2026 Wash Sale Compliance: Common Pitfalls

High-net-worth investors managing multiple accounts face elevated wash sale risk. The rule applies across all accounts you control or accounts controlled by your spouse or a corporation you control. Consider these problematic scenarios:

  • Selling Apple stock in your taxable brokerage account while your 401(k) auto-purchases Apple shares
  • Harvesting losses in your account while your spouse unknowingly buys the same security
  • Dividend reinvestment programs purchasing shares within the 30-day window after you harvest losses
  • Selling equity positions while maintaining call options on the same underlying security

Pro Tip: Create a centralized TLH tracking spreadsheet listing all planned transactions across all accounts. Disable dividend reinvestment 30 days before harvesting losses, and coordinate all trading with your spouse to prevent inadvertent violations.

Strategic Wash Sale Rule Workarounds

Sophisticated investors employ several strategies to capture TLH benefits while navigating wash sale constraints. The most effective TLH examples in 2026 incorporate these approaches:

The “doubling down” strategy: Immediately purchase an equivalent amount of a similar but not substantially identical security when harvesting losses. Hold both positions for 31 days, then sell the original position. This maintains market exposure throughout the wash sale period without triggering the rule.

The sector rotation approach: Replace specific stock positions with broad sector ETFs during the wash sale window. This preserves industry exposure while clearly avoiding substantially identical concerns. After 31 days, investors can rotate back to individual stocks if desired.

The similar ETF swap: Exchange one broad-market ETF for another tracking a similar index from a different provider. For example, swap Vanguard Total Stock Market (VTI) for iShares Core S&P Total U.S. Stock Market (ITOT). Both track the entire U.S. market, but different compositions prevent substantially identical classification.

How Can High-Net-Worth Investors Use TLH to Offset Capital Gains?

Quick Answer: High-net-worth investors use TLH to offset realized gains from real estate sales, business exits, or portfolio rebalancing. This reduces the effective capital gains rate from 23.8% to zero on offset amounts.

For wealthy investors managing substantial taxable portfolios, strategic tax advisory planning coordinates TLH with anticipated capital gains events. The most impactful TLH examples in 2026 involve proactive loss harvesting before major liquidity events such as real estate sales, business dispositions, or large portfolio distributions.

TLH Example 1: Offsetting Real Estate Gains

A real estate investor plans to sell a commercial property in December 2026, generating a $500,000 long-term capital gain. The investor’s current equity portfolio includes $380,000 in unrealized losses accumulated during market volatility.

By systematically harvesting these losses throughout the year before the property sale, the investor offsets $380,000 of the $500,000 gain. This saves approximately $90,440 in federal taxes ($380,000 × 23.8%). The remaining $120,000 gain generates $28,560 in tax liability, far less than the $119,000 tax on the full unshielded gain.

The investor immediately reinvests the proceeds from harvested positions into similar but not substantially identical securities, maintaining market exposure and portfolio allocation targets. After the 31-day wash sale period, the investor can reposition into preferred holdings if desired.

TLH Example 2: Business Owner Stock Concentration

A successful entrepreneur sold their business in 2025, receiving $15 million in after-tax proceeds. Rather than immediately diversifying the concentrated stock position from the acquisition, the owner strategically implements TLH throughout 2026 as part of a multi-year diversification plan.

Each quarter, the owner sells $1 million of the acquirer’s stock (generating gains) while simultaneously harvesting losses from newly established diversified positions. Market volatility provides opportunities to harvest $150,000 to $250,000 in losses quarterly, offsetting a significant portion of diversification gains.

Over three years, this strategy reduces the total tax cost of diversification by $600,000 to $900,000 compared to immediate diversification without TLH. The business owner achieves portfolio diversification while minimizing the tax drag that typically erodes after-tax wealth in these situations.

TLH Example 3: Annual Portfolio Rebalancing

A high-net-worth investor maintains a $10 million taxable portfolio with a target 60/40 stock/bond allocation. During 2026, strong equity performance pushes the allocation to 68/32, requiring a rebalancing sale of approximately $800,000 in equities.

Rather than simply selling winning positions to rebalance, the investor first identifies $220,000 in losses within equity holdings. These losses are harvested and immediately reinvested in similar equities to maintain the 68% equity exposure. Thirty-one days later, the investor executes the full rebalancing transaction, selling winners to reach the 60% target.

The harvested losses offset $220,000 of the rebalancing gains, saving approximately $52,360 in taxes. Without TLH, the $800,000 rebalancing would have generated $190,400 in taxes, but the coordinated strategy reduces this to $138,040—a 27% tax reduction on the rebalancing transaction.

TLH ScenarioCapital GainLosses HarvestedTax Savings
Real Estate Sale$500,000$380,000$90,440
Business Stock Diversification (Quarterly)$1,000,000$200,000$47,600
Portfolio Rebalancing$800,000$220,000$52,360

What Are Multi-Currency TLH Strategies for Global Portfolios?

Quick Answer: Global investors must implement FX-aware lot selection when harvesting losses across currencies. This ensures accurate basis tracking and prevents inadvertent wash sales across foreign exchange positions.

High-net-worth investors increasingly hold international assets denominated in multiple currencies. According to recent wealth surveys, 92% of UK high-net-worth individuals expect increased non-GBP income within three years, highlighting the growing importance of multi-currency tax planning. These global portfolios create additional complexity for TLH examples in 2026.

Currency Gain/Loss Calculations in TLH

When securities are purchased and sold in foreign currencies, U.S. taxpayers must calculate gains and losses in U.S. dollars using exchange rates on the transaction dates. This creates two potential sources of gains or losses: the security’s price movement and currency fluctuation.

Consider an investor who purchased £100,000 of UK stocks when the exchange rate was $1.30/£, investing $130,000. If the stock declines 10% to £90,000 but the pound strengthens to $1.40/£, the position is worth $126,000. Despite the 10% stock decline, the currency gain partially offsets the loss, resulting in only a $4,000 net loss for U.S. tax purposes.

Conversely, if the pound weakens to $1.20/£, the £90,000 position translates to $108,000, creating a $22,000 U.S. dollar loss—far greater than the 10% stock decline suggests. Advanced TLH examples account for these currency dynamics when identifying optimal harvest opportunities.

TLH Example 4: FX-Aware International Equity Harvesting

A wealthy investor holds a diversified portfolio of European equities purchased over multiple years. In 2026, the portfolio shows mixed performance: some holdings have declined in local currency while others have appreciated. However, euro weakness against the dollar creates opportunities for larger U.S. dollar losses than the local currency performance suggests.

The investor employs specific lot identification to selectively harvest positions where both the security declined and the euro weakened relative to the purchase date. A German stock purchased at €50 when the exchange rate was $1.10/€ ($55 cost basis) now trades at €48 with the euro at $1.05/€ ($50.40 current value). The combined 4% stock decline and 4.5% currency decline create a $4.60 per share loss—more than either factor alone.

By targeting these double-loss positions, the investor harvests $175,000 in losses from a $3 million international portfolio despite the underlying securities declining only $95,000 in local currency terms. The currency losses amplify the TLH benefit by 84%.

Digital Asset TLH Considerations for 2026

Cryptocurrency and digital assets add another dimension to TLH strategies. The IRS has extended temporary relief for digital asset reporting through December 31, 2026, allowing alternative identification methods. However, the fundamental wash sale rule does not currently apply to cryptocurrency under existing regulations, creating unique opportunities.

Investors can harvest cryptocurrency losses and immediately repurchase the same asset without triggering wash sale treatment. This enables more aggressive TLH in digital assets compared to traditional securities. However, proposed legislation may close this loophole, making 2026 potentially the last year for unlimited crypto TLH.

Pro Tip: High-net-worth investors with cryptocurrency holdings should maximize TLH opportunities in 2026 before potential regulatory changes. Consult IRS digital asset guidance for current reporting requirements.

How Does TLH Interact with OBBBA Tax Provisions?

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Quick Answer: The One Big Beautiful Bill Act’s permanent $15 million estate exemption and expanded SALT deduction create new TLH coordination opportunities. Strategic planning captures benefits across income, estate, and wealth transfer tax systems.

The OBBBA legislation enacted in July 2025 fundamentally changed the landscape for high-net-worth tax planning. The permanent increase in the estate and gift tax exemption to $15 million per individual ($30 million for married couples) creates substantial wealth transfer planning opportunities that coordinate effectively with TLH strategies.

TLH Example 5: Coordinating Loss Harvesting with Roth Conversions

High-income investors often avoid Roth conversions due to the immediate tax cost. However, TLH creates opportunities to offset conversion income with harvested capital losses, reducing or eliminating the conversion tax burden.

An investor with $2 million in traditional IRA assets plans a $200,000 Roth conversion in 2026. At the 37% ordinary income rate, this creates a $74,000 tax liability. However, the investor’s taxable portfolio contains $185,000 in unrealized losses.

By harvesting these losses in the same year as the conversion, the investor generates $185,000 in capital losses. After offsetting the annual $3,000 ordinary income allowance, $182,000 in losses remain. While capital losses cannot directly offset ordinary income beyond $3,000 annually, the strategic use reduces adjusted gross income calculations for other purposes and provides valuable carryforward losses for future years.

More importantly, the lower AGI from reduced capital gains activity keeps the investor below key income thresholds for the 3.8% NIIT and the temporary $6,000 senior deduction (for those over 65), which phases out above $75,000 for singles and $150,000 for married filing jointly.

TLH Example 6: Gifting Low-Basis Assets After Harvesting Losses

The permanent $15 million exemption enables high-net-worth individuals to make substantial lifetime gifts without estate tax concerns. Strategic TLH enhances the after-tax value of these wealth transfers through basis management.

A wealthy investor plans to gift $5 million in appreciated stock to children. The stock has a cost basis of $1.5 million, creating $3.5 million in unrealized gains. If gifted, the recipient takes the donor’s basis ($1.5 million), meaning future sales trigger substantial capital gains taxes for the recipient.

Instead, the investor harvests $3.5 million in losses from other portfolio positions throughout 2026. The investor then sells the appreciated stock, recognizing the $3.5 million gain but offsetting it entirely with harvested losses. The after-tax proceeds are gifted to children, who receive a “stepped-up” basis equal to the current value, eliminating future capital gains exposure.

This coordinated approach transfers $5 million to the next generation without income tax consequences while preserving the portfolio through immediate reinvestment of harvested positions. The family saves approximately $833,000 in future capital gains taxes that the children would have owed on the low-basis stock.

SALT Cap Interaction with TLH Strategies

OBBBA temporarily increased the state and local tax deduction cap from $10,000 to $40,000 for tax years 2025 through 2029, with phase-outs starting at $500,000 MAGI. For high-net-worth investors in high-tax states, this creates additional incentive to manage income timing through TLH.

By harvesting losses to reduce capital gains, investors in California, New York, or New Jersey can potentially stay under the $500,000 phase-out threshold, preserving the full $40,000 SALT deduction. For a married couple with $525,000 in AGI including $50,000 in capital gains, harvesting $30,000 in losses reduces AGI to $495,000, saving the partial SALT deduction phase-out and reducing both federal and state taxes.

OBBBA ProvisionAmount/ThresholdTLH Coordination Strategy
Estate Exemption$15M individual / $30M marriedHarvest losses before gifting appreciated assets
SALT Cap Increase$40,000 (phase-out above $500k)TLH to reduce AGI below phase-out threshold
Senior Deduction$6,000 single / $12,000 marriedHarvest losses to stay below $75k/$150k phase-out

What Are TLH Timing Strategies for Maximum Benefit?

Quick Answer: Optimal TLH timing depends on market volatility, year-end gains recognition, and strategic coordination with other tax events. Most sophisticated investors harvest losses quarterly and perform year-end reviews.

The timing of TLH activities significantly impacts overall tax efficiency. While losses can be harvested any time during the year, strategic timing maximizes benefits and prevents missed opportunities. The most effective TLH examples in 2026 incorporate systematic review processes rather than ad hoc harvesting.

Quarterly TLH Review Cadence

Professional wealth managers typically review portfolios for TLH opportunities on a quarterly basis, with more frequent monitoring during volatile markets. This systematic approach captures loss opportunities throughout the year rather than waiting until December when many positions may have recovered.

March/April, June/July, September/October, and December reviews ensure comprehensive coverage while respecting wash sale windows from previous harvests. Each quarterly review should identify:

  • Positions with losses exceeding $5,000 (to offset transaction costs)
  • Previously harvested positions now outside the 30-day wash sale window
  • Upcoming gain realization events requiring offset capacity
  • Changes in tax law or personal circumstances affecting optimal strategy

TLH Example 7: Year-End Strategic Positioning

December represents the final opportunity to implement TLH for the current tax year. Sophisticated investors conduct comprehensive year-end reviews in early December, allowing time to execute transactions while respecting settlement timelines. For securities transactions to count in 2026, they must settle by December 31, 2026.

A high-net-worth investor conducts a December 1, 2026 portfolio review revealing $275,000 in realized gains from earlier real estate and stock sales. The portfolio currently holds $340,000 in unrealized losses spread across 15 positions. The investor faces a projected $65,450 tax liability on these gains.

The year-end TLH strategy involves harvesting exactly $275,000 in losses to fully offset realized gains, eliminating the tax liability entirely. Rather than harvesting all available losses, the investor preserves $65,000 in losses for future harvesting, avoiding unnecessary position turnover and maintaining flexibility for subsequent years.

The $275,000 in harvested positions are immediately reinvested in similar but not substantially identical securities on December 1. The investor can reposition back into original holdings after January 1, 2027, or maintain the replacement positions if they perform satisfactorily.

Avoiding December 31 Deadline Pressure

Many investors wait until late December to consider TLH, creating unnecessary pressure and suboptimal execution. Market liquidity typically decreases during the final weeks of December, potentially widening bid-ask spreads and increasing transaction costs.

Additionally, year-end harvesting leaves minimal time to address unexpected complications such as wash sale violations from dividend reinvestment programs or spousal account conflicts. Early December reviews provide three to four weeks to resolve these issues before the December 31 deadline.

Pro Tip: Schedule your year-end TLH review before Thanksgiving. This provides ample time for execution while avoiding holiday market closures and reduced liquidity in late December.

What Are the Compliance Risks with Aggressive TLH?

Quick Answer: The IRS scrutinizes aggressive TLH strategies that lack economic substance or deliberately trigger wash sales. Conservative approaches documenting legitimate investment purposes avoid audit risk and penalties.

While TLH represents a legitimate and encouraged tax planning strategy, the IRS maintains heightened scrutiny of transactions appearing to prioritize tax benefits over genuine investment objectives. High-net-worth taxpayers face elevated audit risk, making compliance and documentation critical components of successful TLH programs.

Economic Substance Doctrine Concerns

The economic substance doctrine requires transactions to have genuine economic purpose beyond tax avoidance. For TLH, this means maintaining legitimate investment rationale for sales and replacements. Red flags include:

  • Selling and immediately repurchasing identical securities (clear wash sale)
  • Excessive trading frequency suggesting tax-driven rather than investment-driven decisions
  • Deliberately engineering losses through related-party transactions
  • Circular transactions designed to manufacture artificial losses

The most defensible TLH examples maintain clear economic purpose: diversification, risk management, sector rotation, or portfolio optimization. Documentation should explain the investment reasoning for each harvest transaction, not merely the tax benefits.

Proper Documentation Requirements

Comprehensive documentation protects investors in the event of IRS examination. Best practices for TLH recordkeeping include:

  • Maintain transaction logs showing purchase date, sale date, and 30-day wash sale compliance
  • Document the investment rationale for replacement securities chosen
  • Preserve brokerage statements showing specific lot identification method used
  • Retain written investment policy statements describing TLH strategy parameters
  • Keep contemporaneous notes from advisory meetings discussing TLH decisions

For foreign securities and multi-currency portfolios, additional documentation proving exchange rates on transaction dates is essential. The IRS may challenge foreign currency gain/loss calculations lacking adequate support.

Penalty Exposure for Wash Sale Violations

Inadvertent wash sale violations typically result in loss disallowance but rarely trigger penalties if reported correctly. However, intentional violations or failures to adjust basis properly can result in:

  • 20% accuracy-related penalty on tax underpayments
  • 40% penalty for gross valuation misstatements
  • 75% penalty for civil fraud in extreme cases
  • Extended statute of limitations allowing examination up to six years

Conservative TLH practices prioritizing wash sale compliance dramatically reduce penalty risk. When uncertain whether a replacement security qualifies as substantially identical, err on the side of caution or consult qualified tax advisors before executing trades.

Compliance Risk LevelTLH PracticeIRS Position
Low RiskETF swap: VOO to SWPPXGenerally accepted, different issuers
Medium RiskSimilar sector ETFsAcceptable if tracking different indexes
High RiskSame stock repurchased within 30 daysClear wash sale violation

 

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Uncle Kam in Action: Real Estate Investor Saves $127K with Strategic TLH

The Client: Michael Chen, a 58-year-old commercial real estate investor with a $25 million net worth, managed a diversified portfolio including multiple rental properties, publicly traded REITs, and a $7 million taxable brokerage account. Michael planned to sell a commercial office building in late 2026, generating an anticipated $950,000 long-term capital gain.

The Challenge: Without planning, the $950,000 gain would trigger $226,100 in federal taxes ($950,000 × 23.8%). Adding California state taxes pushed the total liability above $280,000. Michael wanted to minimize this tax burden while maintaining his investment portfolio’s risk profile and diversification.

The Uncle Kam Solution: Our tax advisory team implemented a comprehensive TLH strategy beginning six months before the anticipated building sale. We conducted a detailed portfolio analysis identifying $645,000 in unrealized losses across Michael’s equity holdings, accumulated during market volatility in 2025 and early 2026.

Rather than harvesting all losses at once, we executed a staged approach over three quarters. In May 2026, we harvested $215,000 in losses from underperforming REIT positions, immediately reinvesting in similar but not substantially identical commercial real estate ETFs. In August, we harvested an additional $220,000 from international equity positions, replacing them with similar emerging market funds from different providers.

Finally, in October—six weeks before the building sale—we harvested the remaining $210,000 in losses from technology sector holdings, rotating into broad-market index funds. Throughout the process, we maintained Michael’s target 65/35 equity/fixed income allocation while respecting all wash sale windows.

When Michael closed on the building sale in November 2026, the $645,000 in harvested losses offset 68% of the $950,000 gain. The remaining $305,000 gain generated only $72,590 in federal taxes—a reduction of $153,510 from the original $226,100 liability.

The Results:

  • Tax Savings: $153,510 in federal taxes avoided through strategic loss harvesting
  • State Tax Benefits: Additional $27,000 in California tax savings
  • Total Tax Reduction: $180,510 (64% reduction from original liability)
  • Investment Advisory Fee: $18,500 for comprehensive TLH planning and execution
  • First-Year ROI: 976% ($180,510 savings ÷ $18,500 fee)
  • Portfolio Impact: Maintained target allocation while improving after-tax returns

Michael’s case demonstrates how sophisticated TLH coordination with major capital events delivers exceptional value for high-net-worth investors. The six-month planning horizon allowed systematic execution without market timing pressure, and the staged approach preserved portfolio diversification throughout the process. View more client success stories demonstrating the power of proactive tax strategy.

Next Steps

Implementing effective TLH examples requires systematic planning, disciplined execution, and ongoing monitoring. Consider these action items for 2026:

  • Schedule quarterly portfolio reviews to identify loss harvesting opportunities before year-end
  • Document your investment rationale for replacement securities to support economic substance
  • Coordinate TLH planning with anticipated gains from business sales or real estate transactions
  • Review all accounts (including spousal and retirement) to prevent inadvertent wash sales
  • Consult with experienced tax strategists to develop comprehensive TLH protocols
  • Evaluate multi-currency TLH opportunities if you hold international investments
  • Consider coordinating TLH with Roth conversions and OBBBA wealth transfer strategies

Frequently Asked Questions

Can I harvest losses in my IRA or 401(k) account?

No, TLH only works in taxable accounts. Retirement accounts like IRAs and 401(k)s grow tax-deferred, so losses within these accounts provide no tax benefit. However, you must monitor retirement account purchases to avoid triggering wash sales on losses harvested in taxable accounts.

How does the wash sale rule apply to ETFs tracking the same index?

ETFs from different providers tracking the same index are generally not considered substantially identical. You can sell Vanguard S&P 500 ETF and immediately purchase iShares S&P 500 ETF without triggering wash sale treatment. The different fund structures and issuers prevent substantially identical classification despite similar holdings.

What happens to harvested losses if I die before using them?

Unused capital loss carryforwards die with the taxpayer and cannot transfer to heirs. This makes it important to harvest losses strategically rather than accumulating unlimited carryforwards. Focus on utilizing losses within reasonable timeframes by offsetting gains or the annual $3,000 ordinary income allowance.

Does TLH work with cryptocurrency in 2026?

Yes, cryptocurrency is treated as property for tax purposes, making gains and losses subject to capital gains treatment. Currently, the wash sale rule does not apply to cryptocurrency under existing regulations. This allows investors to harvest crypto losses and immediately repurchase the same digital assets. However, proposed legislation may eliminate this advantage in future years.

Should I harvest small losses or only focus on large positions?

Focus on losses exceeding $5,000 to ensure tax savings outweigh transaction costs. Small losses under $1,000 rarely justify the administrative burden and trading expenses. Prioritize largest losses first, then harvest medium-sized losses if you anticipate needing additional offset capacity for expected gains.

Can I harvest losses to offset my business income or rental income?

Capital losses only offset capital gains dollar-for-dollar, plus $3,000 of ordinary income annually. You cannot use capital losses to offset business income, rental income, or wages beyond the $3,000 annual limit. However, reducing your overall AGI through TLH can lower your exposure to the 3.8% NIIT on investment income.

How do I report TLH transactions on my tax return?

Report all capital gains and losses on Form 8949, which feeds into Schedule D. Your brokerage provides Form 1099-B showing all sales transactions. You must report each transaction separately, indicating acquisition date, sale date, proceeds, cost basis, and gain or loss. Wash sale adjustments appear in Box 1g of Form 1099-B when your broker tracks them.

Last updated: March, 2026

This information is current as of 3/23/2026. Tax laws change frequently. Verify updates with the IRS or FTB if reading this later.

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Kenneth Dennis

Kenneth Dennis is the CEO & Co Founder of Uncle Kam and co-owner of an eight-figure advisory firm. Recognized by Yahoo Finance for his leadership in modern tax strategy, Kenneth helps business owners and investors unlock powerful ways to minimize taxes and build wealth through proactive planning and automation.

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