How to Do Tax Loss Harvesting (And Avoid Wash Sales)
Lost money on stocks or crypto? Don’t just cry about it. The IRS lets you use those losses to lower your tax bill. Here is how to turn your red numbers into green tax savings (without getting flagged).
Turn Lemons into Tax Credits
It hurts to sell a stock when it’s down 40%. But holding it does nothing for your taxes. Selling it “harvests” the loss for you to use.
| Scenario | Profit/Loss | Taxable Amount |
|---|---|---|
| Scenario A | Won $10k on Tesla | $10,000 Taxable |
| Scenario B | Won $10k / Lost $4k | $6,000 Taxable |
| Scenario C | Won $10k / Lost $15k | $0 Taxable* |
| Goal | Rule |
|---|---|
| Lower Tax | Harvest Loss |
| Stay Safe | Watch 30 Days |
Warning: The “Wash Sale” Rule
The IRS is not stupid. They know you want to sell the stock to get the tax break and then buy it right back because you think it will go up. They banned this.
The 30-Day Rule
If you sell a security at a loss and buy a “substantially identical” security within 30 days (before or after), the loss is disallowed.
(Basically, the loss doesn’t count for taxes, and is just added to your new stock’s cost basis).
The Workaround: “Coke vs Pepsi”
You can’t sell Coke and buy Coke.
But you CAN sell Coke and buy Pepsi.
- Bad: Sell Vanguard S&P 500 ETF (VOO) → Buy iShares S&P 500 ETF (IVV). (Too identical).
- Good: Sell Vanguard S&P 500 ETF (VOO) → Buy Vanguard Total Stock Market (VTI). (Similar, but different index).
3 Steps to execute
1. Check Short vs Long Term
Short-term losses are more valuable because they offset high-tax short-term gains first. Prioritize selling losers you’ve held for less than a year.
2. Sell the Loser
Log into your brokerage (Robinhood/Fidelity) and sell the position. The loss is now “Realized.”
3. Buy the Replacement (Immediately)
Don’t sit in cash if you think the market will recover. Buy a similar but different ETF or competitor stock immediately.
Example: Sold Home Depot? Buy Lowe’s.
Does this apply to Crypto?
It’s complicated. Historically, the “Wash Sale Rule” only applied to “securities” (stocks), and crypto was considered “property.” This was a massive loophole.
However, tax laws are tightening in 2026. Safe Advice: Assume the Wash Sale rule DOES apply to crypto to avoid an audit nightmare. Don’t sell Bitcoin and buy Bitcoin 5 minutes later. Swap Bitcoin for Ethereum if you must.