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Leveraging stock losses for tax savings

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  • Tax-loss harvesting allows investors to offset taxable gains by selling underperforming investments.​
  • The IRS permits a $3,000 annual deduction for net capital losses, with excess losses carried forward.​
  • Adherence to the wash-sale rule is crucial to ensure the deductibility of losses.​

[UNITED STATES] As 2025 unfolds, investors facing stock market downturns can transform these setbacks into financial advantages through a strategy known as tax-loss harvesting. By selling underperforming investments to offset taxable gains, individuals can reduce their tax liabilities and potentially enhance their after-tax returns. This approach is particularly beneficial for those with taxable investment accounts and can be a valuable tool for year-end tax planning.​

Tax-loss harvesting involves selling securities that have declined in value to realize a loss. These realized losses can then offset capital gains from other investments, thereby reducing the amount of taxable income. For instance, if an investor sells a stock at a $5,000 loss and another at a $2,000 gain, the net taxable gain becomes $3,000. This strategy is most effective when applied to taxable accounts, as tax-advantaged accounts like 401(k)s and IRAs are not subject to capital gains taxes.

Recent volatility in sectors such as technology and cryptocurrency has prompted more investors to explore tax-loss harvesting as a proactive measure. According to data from Fidelity Investments, there was a 28% year-over-year increase in the number of retail investors using tax-loss harvesting tools in 2024. Analysts suggest that heightened market uncertainty, along with rising interest rates, has made investors more conscious of strategies to protect their net returns.

Key Considerations and Limitations

Annual Deduction Limits: The IRS allows taxpayers to deduct up to $3,000 ($1,500 if married and filing separately) in net capital losses against ordinary income each year. Any losses exceeding this amount can be carried forward to offset future gains.

Wash-Sale Rule: To prevent taxpayers from claiming a tax benefit on a loss while still maintaining their investment position, the IRS enforces the wash-sale rule. This rule disallows a deduction if the same or a substantially identical security is purchased within 30 days before or after the sale.​

The wash-sale rule, however, does not apply to cryptocurrency holdings under current IRS guidance. This loophole—subject to possible legislative change—allows investors to sell digital assets at a loss and immediately repurchase them, capturing the tax benefit without being penalized. Financial experts caution that while this is technically legal under existing law, it is under increasing scrutiny by regulators and could change in future tax code revisions.

Tax Bracket Impact: The benefits of tax-loss harvesting are more pronounced for individuals in higher tax brackets. Those in lower brackets may find the immediate tax relief less significant, but the strategy can still be advantageous if they anticipate higher future earnings.

It’s also worth noting that tax-loss harvesting can be paired with other tax-efficient strategies like asset location and charitable giving. For instance, while harvesting losses in taxable accounts, investors may simultaneously donate appreciated assets to charities to avoid capital gains taxes and receive a deduction. This type of coordination can further optimize one’s overall financial plan, especially for high-net-worth individuals.

Strategic Tips for Effective Tax-Loss Harvesting

Monitor Portfolio Regularly: Instead of waiting until year-end, investors should review their portfolios quarterly to identify potential losses that can be harvested.​

Avoid Substantially Identical Securities: When replacing sold securities, ensure the new investments are not substantially identical to avoid triggering the wash-sale rule.​

Consult Professionals: Engaging with tax advisors or financial planners can provide personalized strategies and help navigate complex tax regulations.​

Several robo-advisors and wealth management platforms now offer automated tax-loss harvesting features, making the strategy more accessible to everyday investors. Services such as Betterment and Wealthfront automatically scan portfolios for tax-loss harvesting opportunities, often on a daily basis. While convenient, experts recommend reviewing these automated strategies periodically to ensure they align with individual tax goals and investment objectives.

Incorporating tax-loss harvesting into a broader investment strategy requires careful planning and recordkeeping. Investors should maintain detailed documentation of trades, cost basis, and adjusted holdings to simplify tax reporting and avoid compliance issues. Many brokerage platforms provide downloadable tax-loss reports, but it’s still prudent to verify information and consult a CPA, especially when carrying losses forward over multiple years.

Tax-loss harvesting offers a strategic opportunity for investors to mitigate tax liabilities and optimize their investment portfolios. By understanding the rules and timing of this strategy, individuals can make informed decisions that benefit their long-term financial goals. As always, consulting with financial professionals is recommended to tailor strategies to individual circumstances.​


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