Quick Read
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Roth withdrawals turn taxable and trigger a 10% penalty unless you're 59½ and five tax years have passed since your first Roth contribution.
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Each Roth conversion starts its own five-year penalty clock, so a recent conversion can trigger penalties even in a decades-old account.
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Generating $6,150 monthly requires roughly $776,000 in a seven-holding portfolio yielding about 10%, led by FSK and GPIX .
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Read More: Learn 7 ways to generate income with a $1,000,000+ portfolio (sponsor)
A retiree spends two decades building a Roth account, retires at 57, and starts taking $6,150 a month in dividends. In January, the custodian mails a Form 1099-R with code J in box 7.
That code flags an early Roth distribution with no known exception. It puts $73,800 a year of supposedly tax-free income in front of the IRS.
How a Roth Withdrawal Turns Taxable
A Roth payout is fully tax-free only when it counts as a qualified distribution. Two things have to be true. First, you're at least 59½, disabled, or the money goes to your heirs. Second, five tax years have passed since the first year you added to any Roth IRA.
Fail either test, and the IRS uses ordering rules. Your regular contributions come out first, then conversions, then earnings (26 U.S.C. § 408A; IRS Pub. 590-B). Dividends you reinvested count as earnings. So once you've taken out more than you put in, the extra is taxable. If you're under 59½ with no exception, you also owe a 10% additional tax.
Every conversion also runs its own five-year clock for that penalty, which is why timing conversions during the quiet tax years before RMDs begin matters so much (we sized up that window in a free Roth guide here). A recent conversion can set off the penalty even in a Roth you opened decades ago. Withdrawals that aren't qualified get reported on Form 8606.
Learn 7 Ways To Generate Income With A $1,000,000+ Portfolio
If you've saved over $1,000,000, this guide is for you. The last thing you want in retirement is to run out of money, you want your money to generate lasting income while you enjoy your life.
Now you can learn the strategies wealthy retirees use to fund their retirement with The Definitive Guide to Retirement Income from Fisher Investments. Download the guide today! (sponsor)
Three More Ways the Tax-Free Promise Breaks
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If you added more than you're allowed, the IRS charges a 6% excise tax for every year the extra money stays in. Our recent fix-it guide walks through the cleanup.
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You get only one IRA-to-IRA rollover per 1-year period, counted across all your IRAs, Roths included. Trustee-to-trustee transfers don't count toward that limit.
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Say you sell a fund at a loss in a taxable account and buy it in your Roth within 30 days. The IRS rejects the loss and won't add it to your cost basis, so you lose it for good.
What $73,800 a Year Requires
Based on early November 2026 prices, the seven holdings below have a weighted yield of 9.5%. Divide $73,800 by that yield, and you need about $776,000.
Amplify CEF High Income ETF
Amplify CEF High Income ETF( NYSEARCA:YYY ) is a fund that buys other closed-end funds, which hold things like loans, junk bonds, and energy pipelines. The fund accounts for 10% of the portfolio, yields 14.0%, and supplies about 15% of the income.
Distributions paid each month have fallen from $0.20 in 2013 to $0.12. Its latest filing lists no expense ratio, so check the prospectus for total costs, including the fees inside each fund it owns.
Goldman Sachs S&P 500 Premium Income ETF
Goldman Sachs S&P 500 Premium Income ETF( NASDAQ:GPIX ) holds S&P 500 companies and writes call options against them for extra income. In exchange, it gives up some of the upside. The fund makes up 25% of the portfolio, yields 8.7%, and supplies about 23% of the income. The payout changes every month. The latest was $0.39.
Omega Healthcare Investors
Omega Healthcare Investors( NYSE:OHI ) is a real estate investment trust (REIT) that owns nursing homes and senior housing. The holding represents 15% of the portfolio, yields 5.6%, and covers about 9% of the income.
Omega paid $0.67 per quarter from 2020 into early 2026, then raised it to $0.68. Third-quarter adjusted funds from operations came in at $0.82 a share, which covers the dividend with room to spare.
FS KKR Capital
FS KKR Capital( NYSE:FSK ) works as a BDC, meaning it lends money to midsize private businesses. The fund makes up 15% of the portfolio, its regular payout yields 15.0%, and it supplies about 24% of the income, more than any other holding.
FS KKR cut its regular dividend this year. It paid $0.70 every quarter in 2025, then $0.48, $0.42, and $0.44 in 2026. Net asset value per share dropped to $18.28 from $20.89.
British American Tobacco
British American Tobacco( NYSE:BTI ) sells cigarettes, vapes, and nicotine pouches in more than 170 markets. The stock makes up 15% of the portfolio, yields 5.5%, and covers about 9% of the income. The quarterly payout on its U.S. shares rose to about $0.83 in 2026, up from $0.75 in 2025. The company declares its dividend in pounds, so the dollar amount moves with exchange rates.
PIMCO Corporate & Income Opportunity Fund
PIMCO Corporate & Income Opportunity Fund( NYSE:PTY ) is a closed-end fund that borrows money to buy more bonds. That makes both its income and its losses bigger. The fund represents 10% of the portfolio, pays a 12.7% distribution rate, and supplies about 13% of the income.
It often trades at a premium, meaning you pay more than the bonds inside are worth. When that premium shrinks, you lose money even if the bonds hold their value. Before buying, look at the current premium and leverage.
Invesco Preferred ETF
The Invesco Preferred ETF( NYSEARCA:PGX ) holds preferred shares, mostly from financial companies. The ETF accounts for 10% of the portfolio, yields 7.3%, and supplies about 8% of the income. The payouts are fixed, so the price falls when interest rates rise. Shares are down 11% over five years.
Before Your First Withdrawal
This portfolio needs about $776,000 in the Roth to pay $6,150 a month. Your withdrawals become fully tax-free on whichever comes later: your 59½ birthday, or January 1 of the fifth tax year after the year you made your initial contribution.
Before you take the first dollar, confirm that first contribution year and the date of every conversion with your custodian. That record determines whether your 1099-R shows code Q (qualified) or code J.
Learn 7 Ways To Generate Income With A $1,000,000+ Portfolio
If you've saved over $1,000,000, this guide is for you. The last thing you want in retirement is to run out of money, you want your money to generate lasting income while you enjoy your life.
Now you can learn the strategies wealthy retirees use to fund their retirement with The Definitive Guide to Retirement Income from Fisher Investments. Download the guide today! (sponsor)
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