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Checklist for ETF Tax-Loss Harvesting

Tax-loss harvesting with ETFs is a smart way to reduce your tax bill while keeping your portfolio on track. Here's a quick guide to get started:

  • What is it? Sell investments at a loss to offset capital gains or reduce taxable income (up to $3,000 annually).
  • Why ETFs? ETFs are cost-effective, liquid, and offer many alternatives, making them ideal for this strategy.
  • Key Steps:
    1. Identify Losses: Review your portfolio for ETFs with unrealized losses.
    2. Calculate Tax Savings: Offset short-term losses against short-term gains and long-term losses against long-term gains.
    3. Choose Replacements: Pick similar, but not identical, ETFs to maintain market exposure and avoid wash sales.
    4. Avoid Wash Sales: Don't repurchase the same or substantially identical ETFs within 30 days.

Example: Sell SPY (S&P 500 ETF) and replace it with SCHX (Schwab U.S. Large-Cap ETF).

Pro Tip: Regularly monitor your portfolio for opportunities, especially during market volatility. Tools like Mezzi can help track accounts and avoid wash sales.

Tax-loss harvesting isn’t just for year-end - it’s a year-round strategy to save on taxes and grow your investments.

What is Tax Loss Harvesting and How ETFs Can Help

Pre-Harvest Preparation: Setting the Stage

Before diving into selling ETFs for tax-loss harvesting, it’s essential to lay the groundwork. Taking the time to review your portfolio, estimate potential tax savings, and choose suitable replacement investments can help you execute your strategy efficiently while steering clear of costly errors. Here’s how to prepare.

Review Your Portfolio for Losses

Start by examining your taxable accounts to identify ETFs with unrealized losses. Access your brokerage account and check the "unrealized gains/losses" section. For a deeper dive, expand the "Show lot details" option to analyze the performance of individual purchase lots. This detailed view allows you to use the Specific Identification cost basis method, enabling you to sell only the shares with losses while keeping the profitable ones intact.

Calculate Tax Implications and Savings

Understanding the tax impact is critical to deciding which positions to sell. Losses are applied first to gains with matching holding periods - short-term losses offset short-term gains, and long-term losses offset long-term gains. If your losses exceed your gains, you can deduct up to $3,000 of the excess loss from your ordinary income annually ($1,500 for married couples filing separately). Any leftover losses can be carried forward to future years.

Here’s an example: Suppose you realize a $20,000 short-term capital gain but incur a $25,000 short-term capital loss. The loss offsets the gain entirely, leaving an extra $5,000. Of that, $3,000 can reduce ordinary income, and the remaining $2,000 is carried forward. At a 35% marginal tax rate, this scenario could yield an estimated tax benefit of $8,050.

Keep in mind that tax-loss harvesting resets the cost basis lower, which could lead to a larger taxable gain when you sell the replacement investment later.

Find Replacement ETFs

Choosing the right replacement ETF is crucial to maintaining your market exposure while avoiding a wash sale. Aim for ETFs that are similar but not "substantially identical." For instance, if you sell VTI, you might replace it with a comparable ETF like ITOT.

Here are some popular replacement options:

Asset Class Primary ETF Sold Potential Replacement ETF Index Difference
U.S. Large Cap SPDR S&P 500 ETF (SPY) Schwab U.S. Large-Cap ETF (SCHX) S&P 500 vs. Dow Jones U.S. Large-Cap Total Stock Market Index
International Developed Vanguard FTSE Developed Markets ETF (VEA) iShares Core MSCI EAFE ETF (IEFA) FTSE Developed All Cap ex US vs. MSCI EAFE Index
Emerging Markets Vanguard FTSE Emerging Markets ETF (VWO) iShares Core MSCI Emerging Markets ETF (IEMG) FTSE Emerging Markets All Cap China A Inclusion vs. MSCI Emerging Markets Investable Market Index
Total Bond Market Vanguard Total Bond Market ETF (BND) iShares Core U.S. Aggregate Bond ETF (AGG) Bloomberg U.S. Aggregate Float Adjusted vs. Bloomberg U.S. Aggregate Bond Index

When evaluating replacements, consider factors like expense ratios, liquidity, and how well the ETF fits your broader investment strategy. Reinvesting the proceeds swiftly ensures you maintain market exposure and maximize the tax benefits.

Check Dividend and Distribution Dates

Pay close attention to the ex-dividend dates for both the ETF you’re selling and its replacement. Timing can influence your tax situation and the overall effectiveness of your strategy. Selling just before an ex-dividend date might mean forgoing a dividend payment, while buying just before could result in taxable dividend income. To qualify for favorable tax rates on dividends, you need to hold the ETF for more than 60 days within a 121-day window that starts 60 days before the ex-dividend date. Additionally, factor in the timing of capital gains distributions and remember that ETF trades settle two business days after the trade date (T+2).

Executing Your ETF Tax-Loss Harvesting Strategy

Once you're ready to dive in, it's time to put your ETF tax-loss harvesting plan into action. The process requires precision, quick execution, and careful documentation to ensure compliance with IRS rules.

Document Cost Basis and Transaction Details

Start by gathering all the purchase confirmation statements for your ETFs. You'll need to note the purchase price, date, and any associated fees to calculate your losses accurately. The cost basis - the price you paid for the investment, including brokerage fees - is essential for this step.

Since January 1, 2012, most brokerage firms are required to report your ETF cost basis to the IRS. However, you're ultimately responsible for ensuring the accuracy of the information when filing your taxes.

For each transaction, create a detailed record that includes:

  • The ETF ticker symbol
  • Number of shares
  • Purchase date
  • Original purchase price per share
  • Total cost (including fees)
  • Current market value

Track each purchase lot separately. This level of detail is crucial if you want to use the Specific Identification method to sell only the shares that result in a loss.

If you're missing any details, contact your brokerage for help. Many brokers also provide online tools to calculate your adjusted cost basis, factoring in stock splits, dividends, and fees.

Once your records are in order, you're ready to sell.

Sell ETFs with Losses

To maximize your tax benefits, focus on selling the high-cost lots first. If you're placing orders online, use the "specified lot" method to choose exactly which shares to sell. For phone orders, be explicit with your broker. For example, you might say, "Sell the shares I purchased on July 5, 2012, for $11 each".

Make your trades during regular market hours to ensure you're getting fair pricing. Since ETFs trade like stocks, you have the flexibility to time your transactions throughout the trading day.

Keep a meticulous record of each sale, including:

  • Trade date
  • Settlement date (usually two business days later)
  • Number of shares sold
  • Sale price per share
  • Transaction fees

These records are not just for tax filing - they're also critical for ensuring compliance with wash sale rules.

Buy Replacement ETFs Quickly

After selling, act immediately to purchase replacement ETFs and maintain your market exposure. This step is vital to keeping your portfolio aligned with your investment strategy. Thanks to the ease of trading ETFs, you can often sell one and buy another within the same trading session.

When choosing a replacement ETF, look for one that is similar but not substantially identical to the one you sold. Pay attention to factors like expense ratios, liquidity, and tracking error to ensure the replacement fits well into your portfolio.

Promptly buying replacement ETFs minimizes the risk of missing market movements and helps you stay on track with your asset allocation.

Avoid Wash Sales

The wash sale rule is a critical consideration in tax-loss harvesting. It prohibits you from deducting losses if you repurchase the same or substantially identical securities within 30 days before or after the sale. This creates a 61-day window during which you must avoid triggering the rule.

Be aware that the wash sale rule applies across all accounts you control, including traditional IRAs, Roth IRAs, and even your spouse's accounts. Keeping track of this across multiple brokers can be tricky, so maintaining a detailed trade log is essential. Use it to flag potential wash sale risks and mark your calendar for 30 days after each sale to know when it's safe to repurchase the original ETF.

If a wash sale does occur, the loss isn't gone forever - it gets added to the cost basis of the new investment. While this delays the tax benefit, it doesn't eliminate it entirely.

For investors juggling multiple accounts, platforms like Mezzi can simplify the process. These tools provide a unified view of all your accounts and use AI to alert you to potential wash sale issues, helping you stay compliant.

Advanced Considerations and Wash Sale Prevention

Once you've laid the groundwork for your tax strategy, it's time to delve into more advanced steps to protect your tax benefits. These additional measures will help fine-tune your approach and avoid compliance pitfalls.

Learn the Wash Sale Rule

Understanding the wash sale rule is just the beginning - managing all your accounts to avoid unintentional violations is equally important. The IRS doesn’t clearly define what constitutes "substantially identical" securities, so it’s essential to tread carefully when choosing replacement ETFs. For instance, selling the SPDR S&P 500 ETF (SPY) and quickly buying the iShares Core S&P 500 ETF (IVV) could potentially trigger the wash sale rule since both funds track the same index.

If a wash sale does occur, the disallowed loss is added to the cost basis of the replacement investment. For example, if you sell 100 shares at a $1,000 loss and repurchase them within 30 days at a higher price, the $1,000 loss is disallowed but gets rolled into the cost basis of the new shares, impacting future tax calculations.

Check All Accounts for Compliance

The wash sale rule doesn’t just apply to a single account - it spans all your accounts, including taxable brokerage accounts, IRAs (traditional and Roth), and even your spouse’s accounts. While brokerages are responsible for tracking wash sales within an individual account, it’s up to you to monitor transactions across all accounts to avoid accidental violations.

Start by creating an inventory of every account where you or your spouse might hold the ETF you plan to sell. Check each account for existing holdings in the target ETF or any securities that could be considered substantially identical.

For those juggling multiple accounts across various platforms, tracking these transactions can get tricky. Tools like Mezzi offer a consolidated view of all your accounts and use artificial intelligence to flag potential wash sale risks before they become an issue.

Stop Automatic Investments and Reinvestments

Automated investment features can unintentionally trigger wash sales by repurchasing the same ETF you just sold. Before initiating any tax-loss harvesting trades, make sure to turn off automatic investments and dividend reinvestment for at least 31 days following the sale.

If you participate in an employer-sponsored retirement plan, such as a 401(k), that automatically invests in funds similar to the ETF you’re selling, consider temporarily adjusting those contributions. Alternatively, redirect these automatic investments to purchase a different fund that doesn’t fall under the "substantially identical" category.

Keep automation disabled for the full 31-day period before reactivating it. This simple step can help ensure your tax-loss harvesting strategy stays intact and avoids costly errors.

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Year-Round Tax-Loss Harvesting Tips

Tax-loss harvesting isn’t just a once-a-year task - it’s a strategy you can apply throughout the year. Markets can shift quickly, and staying on top of your portfolio helps you make the most of potential opportunities. By incorporating this practice into your regular investment routine, you can reduce the stress of last-minute adjustments during tax season.

Schedule Regular Portfolio Reviews

Creating a consistent schedule to review your portfolio ensures you don’t miss out on tax-loss harvesting opportunities. Many stocks experience significant declines - often dropping by 10% or more - making it possible to identify losses that can translate into tax savings.

A good starting point is to review your portfolio monthly or quarterly, focusing on positions that have dropped 10% or more from your purchase price. These losses are especially valuable during market downturns when declines are more frequent.

For even better results, consider monitoring your portfolio daily. Research shows that daily tax-loss harvesting can generate about 30 basis points of additional annualized tax savings compared to a monthly approach. Even in strong market years, opportunities still arise. For instance, in 2023, while the S&P 500 gained roughly 26%, 22% of its stocks ended the year down by 5% or more.

Set reminders for your scheduled review dates to stay consistent. Making tax-loss harvesting part of your rebalancing routine can save you money over time and improve your after-tax returns. This habit also prepares you to seamlessly maintain your investment strategy with a ready-to-use replacement ETF list.

Keep a List of Replacement ETFs

Having a list of replacement ETFs on hand can save time and help you act quickly when tax-loss opportunities arise. You only need one replacement ETF per asset class, so preparing this list is straightforward.

When building your list, focus on ETFs that meet key criteria: they should have the same structure as your original investment, be easy to trade, offer high liquidity, have a 0.99 correlation with the original security, and be something you’d feel comfortable holding long term.

For example, if you own the Vanguard Total Stock Market ETF (VTI), suitable replacements might include the iShares Total Stock Market ETF (ITOT) or the Schwab US Broad Market ETF (SCHB). Tailor your list based on your specific asset classes, account types, and the investments you hold in your IRAs. Update this list annually to account for new ETFs or changes to existing ones.

If finding suitable replacements feels overwhelming, it might be a good time to reassess your portfolio structure. This process can also help you simplify and improve your overall investment strategy.

Work with a Tax Advisor

While you can handle many aspects of tax-loss harvesting on your own, working with a tax advisor can refine your strategy, especially as your tax situation becomes more complex. A professional can help you integrate tax-loss harvesting with your broader tax plan, ensuring you maximize the benefits without triggering unintended consequences.

For example, a tax advisor can guide you on how harvested losses interact with other taxable events, like capital gains from selling real estate or business transactions. They can also help you align your harvesting strategy with significant upcoming taxable events.

Managing multiple accounts across different platforms adds another layer of complexity. Tools like Mezzi can provide a consolidated view of your accounts and flag potential wash sale risks using artificial intelligence. However, discussing your overall strategy with a tax professional ensures everything works together smoothly.

"Investing requires exposure to volatility for effective tax-loss harvesting. Without it, investors can't use losses to offset taxes. However, realizing these losses only benefits those with enough gains or a high tax rate. Ultimately, the success of this strategy hinges on reinvesting the tax savings wisely to fully capitalize on the benefits." – Thomas Paradise, CFA, Senior Manager in Vanguard's Enterprise Advice group

Reinvesting your tax savings is key to maximizing the benefits of tax-loss harvesting. A tax advisor can help you decide how to reinvest those savings effectively, ensuring they continue to work for you within your portfolio.

Conclusion: Maximizing Your ETF Tax-Loss Harvesting Strategy

A disciplined approach to ETF tax-loss harvesting can help reduce taxes and improve after-tax returns. Success depends on understanding the basics, staying organized, and sticking to a consistent strategy throughout the year.

Main Takeaways

Preparation is key. Before diving into tax-loss harvesting, take time to thoroughly review your portfolio, calculate potential tax impacts, and identify replacement ETFs that align with your investment goals. This groundwork helps you avoid costly mistakes, like triggering wash sale violations.

Timing makes a difference. While many investors wait until year-end for tax planning, taking advantage of opportunities throughout the year can lead to extra savings. For instance, in 2023, when the S&P 500 gained about 26%, 22% of the stocks in the index ended the year down 5% or more. This shows that even in strong markets, there are chances to harvest losses if you stay vigilant.

The wash sale rule is a critical factor. This 30-day rule can disrupt your strategy if ignored. To stay compliant, monitor all your accounts, including IRAs, 401(k)s, and taxable accounts. On average, 30% of stocks finish the year with a negative return, and 75% drop more than 5% at some point during the year. Patience and attention to detail can help you make the most of these opportunities without breaking the rules.

Reinvestment drives long-term success. As Thomas Paradise from Vanguard points out, the real value of tax-loss harvesting comes from reinvesting the tax savings effectively. Reinvesting these savings promptly can amplify your returns over time.

ETFs are a perfect fit for this strategy. Their tax efficiency, low costs, high liquidity, and availability of similar alternatives make them an excellent choice for implementing tax-loss harvesting without disrupting your investment goals.

These takeaways highlight the importance of leveraging tools and technology to simplify execution and enhance results.

How Mezzi Can Help

Mezzi

Managing a tax-loss harvesting strategy can quickly become complex, especially when dealing with multiple accounts, avoiding wash sales, and tracking cost basis. That's where advanced tools like Mezzi can make a big difference.

Mezzi’s AI-powered platform simplifies portfolio management by addressing one of the trickiest parts of tax-loss harvesting: preventing wash sales across multiple accounts. This feature is particularly valuable for investors with assets spread across various brokerages or account types, helping you stay compliant without extra stress.

The platform integrates seamlessly with major U.S. brokerages, consolidates accounts, and provides a unified view of your portfolio. It uses AI to flag wash sale risks, monitor gains and losses, and offer real-time insights into tax implications. This makes it easier to identify opportunities and act on them efficiently.

Additionally, Mezzi’s AI-driven portfolio analysis and tax optimization takes the guesswork out of the process. Instead of manually calculating tax savings or searching for replacement ETFs, you can rely on the platform’s actionable insights to make informed decisions.

For self-directed investors, Mezzi offers a streamlined way to maximize tax-loss harvesting without getting bogged down in the details. By connecting every step - portfolio review, compliance, and reinvestment - the platform focuses on saving time, minimizing risks, and improving tax outcomes. It’s a powerful tool for those looking to execute their strategy effectively and efficiently.

FAQs

What steps can I take to avoid triggering the wash sale rule when using ETFs for tax-loss harvesting?

To steer clear of the wash sale rule when engaging in ETF tax-loss harvesting, here are some practical strategies:

  • Wait at Least 31 Days: If you sell an ETF at a loss, don’t buy back the same ETF - or one that’s considered substantially identical - for at least 31 days. This avoids the wash sale period, which includes the 30 days before and after the sale.
  • Opt for Similar, Not Identical ETFs: Instead of repurchasing the same ETF, consider buying one that tracks a similar index or sector but isn’t classified as substantially identical. This way, you can keep your market exposure without breaking the rule.
  • Pause Automatic Dividend Reinvestment: If you’ve set up an automatic dividend reinvestment plan, make sure to temporarily disable it for the ETF you’ve sold. Reinvesting dividends during the wash sale period could unintentionally trigger the rule.

If your situation is more complicated or you’re unsure about the specifics, it’s a smart move to consult with a tax professional. Their expertise can help you stay compliant while maximizing your tax advantages.

What are the long-term effects of resetting your cost basis with tax-loss harvesting?

Resetting your cost basis through tax-loss harvesting can influence your investments in both immediate and future ways. In the short term, it can help offset capital gains, which reduces your tax bill and may improve your after-tax returns. Plus, it gives you the chance to reinvest in assets that better match your financial objectives.

But don’t overlook the long-term effects. A lower cost basis could lead to higher capital gains taxes down the road if your investments grow significantly and you decide to sell. While tax-loss harvesting is a smart way to improve tax efficiency, it’s crucial to carefully plan and weigh the immediate benefits against the potential future tax impact.

How can I make sure my tax-loss harvesting strategy supports my investment goals and tax planning?

Aligning Tax-Loss Harvesting with Your Investment Goals

Before diving into tax-loss harvesting, take a step back and evaluate your broader financial objectives and risk tolerance. Selling investments solely for tax advantages might throw off your portfolio's balance, especially if it doesn't align with your long-term investment strategy.

When you do decide to harvest losses, make sure to reinvest the proceeds strategically. This helps you maintain your preferred asset allocation while steering clear of wash sales. You could also use the tax savings to boost your portfolio or tackle other financial priorities, such as paying down debt. Keep an eye on your portfolio regularly to ensure it stays aligned with your goals and make adjustments as your financial situation or market conditions evolve.

For a more streamlined approach, tools like Mezzi can be a game-changer. With advanced tax optimization features, it simplifies the process, helps you avoid wash sales, and ensures efficient management of investments across all your accounts.

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