Before the Next Payout: The High-Yield Dividend Bundle to Buy Before November
Five U.S.-listed securities all clear the 5.22% risk-free bar heading into November, but their safety profiles range from rock-solid free cash flow coverage to something far more precarious. Knowing which is which could be the difference between collecting a fat…
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Income investors are already paid well to wait. The 10-year Treasury yield stands at 5.22%, so any dividend payer held into November has to beat that risk-free bar by enough to justify its added risk. The five U.S.-listed securities below all clear it, and each has a payout either scheduled or building before the calendar turns. Their safety profiles are very different, though. Some are covered by free cash flow, and some depend entirely on access to capital markets. That is why this bundle starts with the best-covered payout and works down from there.
Plains All American Pipeline: Raised Payout With Free Cash Flow to Spare
Plains All American Pipeline (NASDAQ:PAA | PAA Price Prediction) pays a quarterly distribution of $0.4175 per unit, or $1.67 annualized. With a recent price of $24.45, that works out to a 6.8% yield, enough to count as ultra-high-yield. Units must be held before the October 30 ex-dividend date to collect the November 13 payment.
Dividend safety: Management raised full-year guidance to roughly $1.85 billion of adjusted free cash flow and $2.88B of adjusted EBITDA. With 705,566,000 units outstanding, that free cash flow covers the annualized distribution about 1.57 times. First-quarter operating cash flow of $418 million easily covered $132 million of capex. The payout has also grown every year since the reset: $0.18 per quarter in 2021, $0.2675 in 2023, $0.38 in 2025, and $0.4175 this year. That rise came after a 2020 cut from $0.36 to $0.18, a reminder that the payout has been reduced before.
Bull case: Permian pipeline volumes rose to 10,039 kbpd from 9,086 kbpd, which lifted Crude Oil segment adjusted EBITDA 4% to $582 million. The completed Cactus III acquisition adds more fee-based throughput. Units trade at about 13 times forward earnings after a 63.74% one-year gain.
Risk: Leverage was 4.1x in the first quarter, above the 3.25x to 3.75x target. Getting back into that range depends on closing the pending NGL sale to Keyera.
AGNC Investment: Steady $0.12 Monthly Checks at a 16.6% Yield
AGNC Investment (NASDAQ:AGNC) declared another $0.12 monthly dividend on October 7. It goes ex-dividend on October 30 and pays on November 10. The annualized $1.44 against an $8.67 share price gives an ultra-high 16.6% yield.
Dividend safety: Second-quarter EPS came in at $0.40, ahead of the $0.38 estimate and above the $0.36 paid out over the quarter. In the first quarter, net spread and dollar roll income reached $0.42 per share. Tangible net book value rose 2.4% to $8.58, and the net interest spread held at 2.00%. The dividend has been $0.12 every month since the 2020-04-29 ex-date. Before that, it stepped down from $0.20 to $0.18 to $0.16, so the overall record reflects relative stability.
Bull case: Management says agency MBS spreads remain elevated versus historically tight corporate bonds, which supports returns on its roughly $97.2 billion portfolio. Shares fell 16.42% over the past month, which raised the yield for new buyers. They now trade at about four times trailing earnings and 1.11 times book. AGNC is also joining the S&P MidCap 400.
Risk: Leverage of about 7.4x, funded with repo borrowing at a 13-day weighted average maturity, means a rate shock can quickly hurt book value. That happened in the first quarter, when tangible book fell 5.6%.
Strategy Stretch Preferred: 12% Paid Twice a Month
Strategy Inc. Variable Rate Series A Perpetual Stretch Preferred (NASDAQ:STRC) has a 12.00% annualized rate, paid as $0.50 semi-monthly payments. At $99.78, the yield on price is about 12.0%, which puts it in ultra-high-yield territory. The October 30 ex-date pays November 15.
Dividend safety: This payout relies on reserves: Strategy Inc. holds a $3.75 billion USD Reserve that covers roughly 2.1 years of preferred dividends and interest. It paid $400.7 million in preferred dividends last quarter. The balance sheet holds 846,000 units of Bitcoin (CRYPTO:BTC), has a market value of $49.7 billion against a $63.9 billion cost basis, along with $6.7 billion of convertible debt. STRC is a recently issued security with no long dividend record. The board raised the rate from 11.50% to keep the shares trading near par.
Bull case: That rate increase is working. Shares sit close to the $100 target par, up from a 52-week low of $68.63. A $1.0 billion repurchase program, with about $975 million left, steps in to buy below par, which gives holders a defined source of price support.
Risk: Dividend coverage depends on Strategy Inc.’s continued access to equity markets. A sharp drop in Bitcoin could shrink that access. The second quarter’s $8.22 billion GAAP net loss came almost entirely from unrealized Bitcoin losses.
Strive Series A Preferred: 13% Paid Every Business Day
Strive Variable Rate Series A Perpetual Preferred (NASDAQ:SATA) pays cash every U.S. business day at a 13.00% annualized rate, an ultra-high yield on a perpetual preferred trading at $99.46. Daily payments began June 16, so income keeps arriving through November without a single ex-dividend date to plan around.
Dividend safety: Strive is debt-free, with zero pledged Bitcoin and no margin requirements. It held $87.6 million in cash plus a $48.0 million position in STRC, against $26.2 million of SATA dividends declared in its latest quarter. That cash covers several quarters of payouts, but operating earnings cover none of it: the latest non-GAAP loss was $3.65 per share. The daily-dividend record goes back only a few months.
The bull case is straightforward: the Semler Scientific merger raised Bitcoin holdings to 15,009 BTC. With no debt on the balance sheet, no lenders hold claims that rank ahead of SATA. Shares are up 16.77% over the trailing year, and the firm manages more than $2.7 billion in client assets.
Risk: Funding the dividend over time depends on issuing more stock and monetizing Bitcoin, so shareholders face ongoing dilution, and any Bitcoin decline hits Strive directly.
ETRACS Crude Oil Shares Covered Call ETN: Biggest Checks, Least Predictable
ETRACS Crude Oil Shares Covered Call ETN (NASDAQ:USOI) paid $23.9829 over the trailing 12 months. Against a $46.23 price, that is a 51.9% trailing yield. The next distribution of $3.1386 goes ex on October 21 and pays October 26, the first check in this bundle.
Dividend safety: Payouts depend on option income: distributions come from premiums on covered calls written against a crude oil fund. Monthly amounts in the record have ranged from $0.3835 to $7.4743. The “balance sheet” that matters is the issuer’s: the note is an unsecured obligation on the UBS platform that absorbed Credit Suisse, and it matures in 2037. Payments have arrived monthly without a gap in the available history.
Bull case: Volatile crude markets produce higher option premiums. The EIA’s May outlook put third-quarter WTI at an average of $90.06. The note has gained 49.89% year to date, so recent holders have received both income and price gains.
Risk: The same EIA outlook projects WTI falling to $83.00 in the fourth quarter and averaging $74.39 next year. Calmer, lower oil prices would mean smaller premiums and gradual erosion of the note’s value.
Ranking the November Payouts by Safety
Plains All American has the best-covered payout in this group, backed by free cash flow that clears its distribution about 1.57 times. AGNC adds monthly income with earnings that currently exceed the dividend. Both Bitcoin-linked preferreds and USOI offer bigger stated yields, but each relies on outside funding sources: equity markets for Strategy Inc. and Strive, and oil volatility for USOI. A double-digit yield almost always signals that the market suspects something, and we listed the seven warning signs that a payout is about to be cut in a free dividend trap guide here. Plains and AGNC have the strongest coverage in this group, while the other three pair higher yields with greater funding risk.
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Lee Jackson has covered Wall Street analysts' equity and debt research and equity strategy daily for 24/7 Wall St. since 2012. His broad, diverse career, including a stint as creative services director at an NBC affiliate in Austin, Texas, gives him unique insight into the financial industry.
Lee Jackson's journey in the financial industry spans more than 30 years, including nearly two decades as an institutional equity salesperson at Bear Stearns, Lehman Brothers, and Morgan Stanley. His career spanned pivotal sell-side Wall Street events, from the dot-com rise and bubble to the Long-Term Capital Management debacle, 9/11, and the Great Recession of 2008. This reflects his resilience and adaptability amid market volatility.
Lee Jackson’s practical financial industry experience, gained through a career at some of the biggest banks and brokerage firms, is complemented by a lifetime of writing across various platforms. This unique combination allows him to shed light on the intricacies of Wall Street in a way only someone with deep insider experience and knowledge can. Moreover, his extensive network across Wall Street continues to provide direct access for him and 24/7 Wall St., a privilege few firms enjoy.
Since 2012, Jackson’s work for 24/7 Wall St. has been featured in Barron’s, Yahoo Finance, MarketWatch, Business Insider, TradingView, Real Money, The Street, Seeking Alpha, Benzinga, and other media outlets. He attended the prestigious Cranbrook Schools in Bloomfield Hills, Michigan, and has a degree in broadcasting from the Specs Howard School of Media Arts.
