Are your crypto gains long-term or short term? (If you held the crypto for more than one year before selling it, it's long-term.) If long-term, check the long-term capital gains brackets to see if you're actually going to owe tax on any of it, since the first LTCG bracket is taxes at 0%. If you would pay actual tax on your gains (either because some or all of your income is above the 0% bracket, or because some or all of your gains are short-term), then you can certainly consider harvesting losses. Whether it makes sense to do so is a complicated question. Do you think the stocks will turn around? Do you need the money sooner rather than later? What rate will your gains be taxed at, and would you rather "save" your losses for a later year (if you think they'll stay down)? It's not a super simple thing to answer, unfortunately (unless your gains would all be taxed at 0% & you don't need the money from your losses right now, in which case no reason to harvest those losses now). Answer from sorator on reddit.com
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Charles Schwab
schwab.com › learn › story › 4-reasons-to-sell-your-losers
4 Reasons to Sell Your Losers | Charles Schwab
If you don't want to sell your winners prematurely, it might make more sense to generate the necessary income by selling your losers—which may allow you to offset up to $3,000 a year in ordinary income in the process.
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Investopedia
investopedia.com › investing › selling-a-losing-stock
10 Reasons to Sell a Losing Investment Before It's Too Late
November 6, 2025 - Technical analysis offers a systematic approach to selling losing positions by focusing on price movements, trends, and market signals. Key indicators such as the breakdown of support levels, trend reversals, bearish chart patterns, declining volume, and overbought or oversold conditions can signal when a security, such as a stock, is likely to continue declining, prompting a sale.
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Reddit
reddit.com › r/tax › is it better to sell some stocks at a loss to offset gains before next year?
r/tax on Reddit: Is it better to sell some stocks at a loss to offset gains before next year?
November 15, 2025 -

I have about $10k realized gains from crypto this year, but I also hold some stocks that are down. Should I sell some of those stocks at a loss to offset the crypto gains? Or just keep holding and pay taxes on the 10k?

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Investing News Network
investingnews.com › home
Mark These Tax-loss Selling Dates on Your Calendar | INN
3 weeks ago - Buying stocks low and selling them high is ideal, but sometimes investments go sour. In such cases, all hope is not lost — at the end of the year, investors can sell investments that provided losses instead of capital gains.
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Kiplinger
kiplinger.com › home › investing
How Selling a Losing Stock Position Can Lower Your Tax Bill | Kiplinger
December 17, 2024 - It would be a shame to end up paying more taxes than you need to because you got impatient and jumped the gun on a washed sale. Tax-loss harvesting doesn't have to be something you only do at the end of the year.
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Merrill
ml.com › articles › selling-high-performing-stocks-3-ideas-to-help-minimize-capital-gains-taxes.html
Selling Stocks and Bonds: How to Avoid Capital Gains Taxes
June 30, 2025 - With an investment that has performed strongly, you might, for example, sell a portion at the end of 2025, another part in 2026 and the remainder early in 2027. That way, you complete the sale in a little over 12 months while spreading potential ...
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The Motley Fool
fool.com › investing › how-to-invest › stocks › when-to-sell-stocks
When to Sell Stocks: 5 Reasons to Sell a Stock | The Motley Fool
May 14, 2025 - It's generally a best practice not to invest in the stock market with any money you expect to need within the next few years. But if you need the money, that's certainly a valid reason to sell. Perhaps you want to purchase a house and sell some stock to cover the down payment.
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Vanguard
investor.vanguard.com › home › investor resources & education › tax forms & information › maximize your tax savings with tax-loss harvesting
Tax-loss harvesting explained | Vanguard
So, if you know you're going to ... to offset them. For example, if you need to rebalance your accounts, you could sell shares of funds or stocks that have lost value since you purchased them....
Find elsewhere
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Bankrate
bankrate.com › investing
How To Know When To Sell A Stock For A Profit — Or A Loss | Bankrate
September 23, 2025 - There’s an old saying that no one ever went broke taking a profit, but selling just because a stock has gone up isn’t a sound investment practice. Some of the world’s most successful companies are able to compound investors’ capital for decades, and those who sell too soon end up missing out on years of future gains.
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RegionsBank
regions.com › home › insights › wealth insights › investments & markets › when to consider selling your stocks at a loss
When to consider selling your stocks at a loss | Regions Bank
So-called tax-loss harvesting occurs when investors sell underperformers and use the resulting capital losses to offset capital gains achieved on other sales during the year, ultimately reducing their overall income tax bill for the year. “If we had our way, none of the stocks or investments our clients own would have losses at all, but we understand that’s not realistic,” Chenoweth says. “Tax-loss harvesting allows anyone to make the best of a bad situation.” · Sometimes, it’s best not to sell at all. Energy stocks, for example, scuffled from 2014 to 2020, especially toward the end of that period as the coronavirus pandemic crimped the global economy.
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Investopedia
investopedia.com › articles › personal-finance › 100515 › heres-how-deduct-your-stock-losses-your-tax-bill.asp
Maximize Tax Savings by Deducting Stock Losses
October 13, 2025 - It's generally better to take any ... your total ordinary income tax rate. Don't try selling a stock at the end of the year to get a tax deduction and buy it right back in the new year....
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Quora
quora.com › When-is-it-beneficial-to-sell-stocks-at-a-loss-for-tax-purposes-instead-of-taking-advantage-of-the-losses-immediately
When is it beneficial to sell stocks at a loss for tax purposes instead of taking advantage of the losses immediately? - Quora
If a stock sale represents a loss, it does so on May 16th or August 7th or December 30 of the same year. Most active traders get rid of losers ASAP because they do not want to see their goof on their screen for months and they prefer to r...
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Quora
quora.com › Should-I-sell-my-loser-stock-at-the-end-of-the-year-and-reduce-my-profit-or-should-I-carry-my-loss-to-the-next-year
Should I sell my loser stock at the end of the year and reduce my profit or should I carry my loss to the next year? - Quora
Answer (1 of 5): Loser stock? Honestly? Are you sure you are cut out for this? Because it does not sound like it. Not to me. Stocks are long term duration assets. I will give you an example of a stock that has been in the news lately. Maybe then you will begin to understand. I first bought ...
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Is it better to realize the loss and buy back in at the lower price or just hold it?

I'm not a big fan of hypothetical questions. It depends on what you're trying to optimize for, i.e. taxes or total return. Most investment advisors would tell you "don't let the tax tail wag the investment dog."

There's an opportunity cost to selling with the intent to buy back in at a lower price. What if it recovers as quickly as it dropped? What if it drops further?

Time in the market generally beats timing the market. If you liked the stock at $150 and intend to hold it indefinitely, you should love it at $100 and consider buying more instead of selling.


Adding my comment to the answer:

You can't realistically assume that you're selling and buying at the same price.

Even if you did, what's the point? If you're selling/buying near instantaneously the loss will be disallowed due to the wash sale rule, which prohibits selling an investment for a loss and replacing it with the same or a "substantially identical" investment 30 days before or after the sale.

If you wait long enough, it's virtually impossible to buy back in at the same price. At a minimum, you're crossing the bid-ask spread.

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If you're asking about taxes, you'd need to specify a country. If you're in the US (based on your profile), you'd have a wash sale unless you bought the shares back more than 30 days later in which case you wouldn't be allowed to deduct the capital loss. So in the US, unless you want to exit the position and stay out for more than 30 days before buying the shares back, you're better off holding the shares.

If you are willing to stay out of the position for more than 30 days, then it can be reduced to a math problem. But you'd need to make guesses about things like what the capital gains tax rate will be when you sell, what discount rate to apply to get the present value of future cash flows, etc. And if you're thinking of holding the shares until you die, potentially you'd never owe capital gains tax...

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RBC Wealth Management
rbcwealthmanagement.com › home › insights › tax-loss selling – building a better understanding
Tax-loss selling – building a better understanding
November 1, 2023 - The 2016 official deadline for ... strategy, that’s not to say it’s the only time. Opportunities for selling at a loss should be considered throughout the year....
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Reddit
reddit.com › r/stocks › would you sell a stock you have over 90% loss? or hold?
r/stocks on Reddit: Would you sell a stock you have over 90% loss? Or hold?
October 19, 2024 -

3 stocks I bought during the COVID era, Shift Tech, charge point and blink charging. All these stocks bombed even tho EVs are taking off. Do I cut and run, or just hold since I've already held this long?