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ESPP are typically bought at a discount, the discount is taxed as ordinary income. The remaining gains are taxed as long term cap gains when held for over 2 years. Depending on your income during retirement, that can be 0%, up to 15% maximum. That’s not too bad.


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Yes, you will owe capital gains tax. Even if you sold and then re-purchased the shares within the same account, the answer would be the same. The only reason capital gains are not taxable is if they occur within a tax-advantaged account like a 401(k) or IRA. Additionally, there is something called a wash sale that prevents you from realizing a capital loss ...


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