Investing Insights18 Juli 2025

This Dividend Investing Strategy Deserves a Second Look

Amy Arnott, portfolio strategist for Morningstar Inc., discusses how a popular dividend investing strategy works, and who would or wouldn’t benefit from it.

On this episode:

Let’s focus on when dividend reinvesting works as a strategy and when it does not. Who should consider reinvesting dividends?
When shouldn’t an investor reinvest their dividends?
Are there any differences between reinvesting dividends in a taxable vs a tax-deferred account?
What types of dividends are taxable and non-taxable?

This part of the episode includes a correction: A response about which dividends are taxable versus nontaxable should have said, “If you're in a bond fund, most dividends would be taxable unless you’re investing in Treasury bonds, which would normally be exempt from state and local taxes.” We incorrectly said federal taxes.

How long you’ve owned a dividend-paying stock matters when it comes to taxes. Can you explain the differences between qualified and non-qualified dividends?
What kind of record-keeping does reinvesting dividends require, and how does reinvestment affect the cost-basis?
How are considerations different for stock dividends vs fund dividends?
What’s the final takeaway for the audience about dividend reinvestment?

Read about topics from this episode.

When to Reinvest Dividends (or Not)

These 4 Dividend ETFs Strike the Right Balance for Income Investors

10 Top Dividend Stocks for 2025

13 Elite Companies With Fast-Growing Dividends

What Are Dividends?

The 10 Best Dividend Stocks

The Best Dividend Funds

What Makes a Great Dividend Fund?

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Read what our team is writing:

Amy C. Arnott

Ivanna Hampton

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