A board above the trading floor of the New York Stock Exchange displays the closing number for the Dow Jones industrial average, Thursday, Dec. 11, 2025. Richard Drew/AP
I recently dug into the pros and cons of dividend reinvestment. Readers of the article sent me questions about other dividend-related topics. Here are some of the most common questions I got:
What Should I Know About Reinvested Dividends and Wash Sales?
Reinvesting dividends means purchasing additional shares, which can complicate sales or tax-loss harvesting in taxable accounts. The IRS’s wash-sale rules prohibit claiming a tax loss after a sale if you’ve purchased the same or “substantially identical” security 30 days before or after selling. You could wait at least 30 days after a dividend before selling, and make sure to sell at least 30 days before the next dividend, but to reduce hassle, it’s probably best not to reinvest dividends for holdings that you plan to sell soon.
If I Reinvest Dividends, Will I End Up With Fractional Shares That Are Difficult to Sell?
Reinvesting dividends typically means purchasing small amounts that get added to your existing stock/fund position. You’ll probably end up with fractional shares, where you own only part of a share. Most major brokerages let you sell fractional shares, but you typically need to sell fractional shares as a market order, and liquidating fractional shares may take an additional day.
How Are Dividends Taxed?
For stocks and stock funds, the tax rate depends on whether the dividend is qualified or nonqualified (also called ordinary). Dividends are qualified if you meet the 60-day holding requirement within a 121-day window around the ex-dividend date; these are taxed at capital gains rates—zero percent or 15 percent for most people. Others are taxed as ordinary income. Dividends from holdings that don’t meet these requirements are nonqualified and are taxed as ordinary income.
Bond or bond fund payments are considered interest income and are typically taxed as ordinary income. Income from Treasury bonds is exempt from state and local taxes, and income from municipal bonds is usually exempt from federal, state, and local taxes, depending on the issuer’s location.
Are Reinvested Dividends Taxable?
As I mentioned in another article, dividends for holdings in taxable accounts are taxable whether taken in cash or reinvested. If you reinvest dividends, you’ll need to add each dividend to the holding’s cost basis. You could end up with many separate tax lots with different cost-basis levels. When you sell the stock, you’ll need to match each sale with a specific tax lot.
Are Stocks That Pay Dividends Better?
Money is fungible—it doesn’t matter whether you receive it as income or capital appreciation. A company’s value shouldn’t depend on whether it pays a dividend. However, behavioral finance researchers have found that many investors perceive dividends as more stable and predictable than capital gains. Tax issues are another important consideration.
How Do Dividend-Oriented Strategies Perform in a Recession?
Dividend stocks historically hold up well during economic slowdowns and can provide downside protection in drawdowns. However, funds that focus on high-yield stocks without incorporating quality screens tend to be more exposed to economically sensitive sectors, and companies that may not be able to keep paying dividends during recessions.
Can I Live Off My Portfolio’s Dividends and Interest Income in Retirement?
Some investors like this approach. Dividends can create steady income similar to a regular paycheck, and many investors like the idea of leaving their principal untouched. However, it can be tough to create a portfolio that generates enough yield for an income-only approach, especially one that keeps pace with inflation.
