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What is a Dividend Rollover Plan?

A dividend rollover plan, also known as a dividend capture strategy, is an investment approach that aims to generate short-term income for investors. This strategy involves purchasing a dividend-paying stock shortly before its ex-dividend date and then selling the shares shortly after the dividend is paid. While the dividend rollover plan may seem straightforward, there are risks involved that investors need to consider. In this article, we will explore the concept of a dividend rollover plan, discuss its workings, analyze the associated risks, and provide insights into its tax implications.

Understanding the Dividend Rollover Plan

A dividend rollover plan is an investment strategy designed to produce short-term income. The basic premise is to buy a dividend-paying stock shortly before its ex-dividend date, allowing the investor to capture the upcoming dividend payment. The investor then sells the shares after the dividend has been paid, aiming to secure a short-term income stream.

However, the success of a dividend rollover plan is not guaranteed. In most cases, the price of a dividend-paying stock tends to decline by an amount equal to the dividend payment after the dividend is paid. This decline can offset the gain from the dividend, resulting in a break-even or even unprofitable transaction when accounting for trading fees and tax implications.

Implementing a dividend rollover plan involves several steps. First, the investor selects a stock with an upcoming dividend and purchases it before the ex-dividend date. The investor can sell the stock on or after the ex-dividend date but not before. The dividend is then assigned on the date of record, and finally, the dividend is paid out on the pay date.

It's important to note that this strategy is tax-heavy, and investors should consider using a no-commission broker, preferably within a tax-sheltered retirement account, to minimize costs and tax liabilities.

Analyzing Risks and Considerations

Investors utilizing a dividend rollover plan should be aware of the risks involved. While capturing the dividend payment can be enticing, there are several factors to consider that could impact the profitability of the strategy.

Firstly, the post-dividend share price movement plays a crucial role. If the share price declines after the dividend payment, the investor may secure a small loss on the sale of shares, negating the gain from the dividend. Even a minor variance in the post-dividend share price can render the transaction unprofitable on a net basis, considering trading fees and taxes.

Additionally, market factors and unexpected news unrelated to the dividend can affect share prices, introducing further uncertainty. Prudent investors demand a risk premium to compensate for the unpredictability of share price movements.

To mitigate risk, investors should carefully select companies with a history of consistent post-dividend price movements that suggest the strategy will likely be viable. Thorough research and analysis are necessary to identify stocks that align with the dividend rollover plan.

Tax Implications of a Dividend Rollover Plan

Tax considerations are a crucial aspect of implementing a dividend rollover plan. Dividends captured through this strategy are typically classified as unqualified dividends. To qualify for the preferential tax treatment of qualified dividends, dividends must be held for a minimum period of 60 days before the ex-dividend date.

Unqualified dividends are subject to income tax rates, which can significantly impact the overall profitability of the dividend rollover plan. However, investors can potentially avoid taxes on dividends by executing the strategy within a tax-sheltered retirement account, such as an Individual Retirement Account (IRA).


Dividend rollover plan is another, rarely used way to refer to a Dividend Reinvestment Plan (DRIP).

Unfortunately just reinvesting dividends in a systematic way will not get you out of any tax implication associated with the dividends attributed to your account. An automatic dividend reinvestment plan (DRIP) is an option in some investment accounts and financial products. Any dividends paid out will be reinvested in the same mutual fund, ETF, or stock at the earliest possible opportunity.

Most companies who pay regular dividends do so on a quarterly basis, so you’ll be buying shares a few times a year with a DRIP. This can be good, following the logic of Dollar Cost Averaging (DCA), which suggests that investing incrementally instead of in one lump sum will have higher probability of getting a better average price per share.

Dividend-paying companies have strong historical returns, especially when dividends are reinvested. Without reinvesting, you miss out on the compounding effect that the dividends would add. Dividends will still be taxable to the investor every year if they are not part of a tax-deferred account such as an IRA.

They tend to be taxed a short-term capital gains rates, which is effectively the investor’s income tax bracket.

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