The Clock Is Ticking: 3 High-Yield Dividend Stocks With Deadlines This Week

Three high-yield income names share one deadline this week. Plains All American Pipeline (NASDAQ:PAA | PAA Price Prediction), a First Merchants (NASDAQ:FRME) preferred issue, and Union Bankshares (NASDAQ:UNB) each lose their dividend eligibility on October 30, 2026, and all three pay in November. To collect the upcoming checks, buyers must own the shares through the close on October 29.

How the timing works: You must own the stock before the ex-dividend date to collect the payment. If you buy on or after the ex-date, the seller gets that payment. The pay date is just when the cash arrives.

Plains All American Pipeline (PAA): A 6.3% Yield That Grew This Year

Plains declared a distribution of $0.4175 per unit on October 1. Units go ex on October 30, and the payment date is November 13, so the last day to buy is October 29. The $1.67 annualized rate on a $26.50 unit price gives a forward yield of 6.3%.

For an MLP, the right test is distributable cash flow. Operating cash flow serves as a practical proxy. In 2025, Plains generated $2.936 billion in operating cash flow and paid $1.295 billion in distributions, or 44.1% of that cash. After $643 million in capex, what remained covered distributions 1.77 times. The quarter ended June 2026 was better, with $955 million of operating cash against $346 million paid out (2.76x). The March quarter was closer: $418 million against $348 million.

The high yield pairs with a rising unit price. The units are up 70.61% over the past year, and the quarterly rate rose 9.9% from $0.38. There are risks, though. Earnings missed estimates in each of the last two reported quarters. Financing for the EPIC Crude acquisition cut pro forma 2025 earnings per unit to $1.01 from $1.12. And Plains cut its distribution to $0.18 from $0.36 in 2020, a reminder that a past cut is one of the warning signs we cataloged in a free guide to spotting dividend traps before the next one.

First Merchants Series A Preferred (FRMEP): A 7.50% Coupon Near Par

First Merchants 7.50% Non-Cumulative Perpetual Preferred, Series A (NASDAQ:FRMEP) depositary shares will pay $0.4688 per share. The company declared the payment on October 15; shares begin trading without the dividend on October 30, and it pays on November 16. The indicated annual payout is $1.8752. Over the past year, the shares traded between $23.89 and $26.51. At the $25.21 50-day average, that payout works out to about 7.4%.

The preferred is paid out of the parent bank’s earnings, so coverage comes down to the bank’s profits. In the third quarter, First Merchants posted GAAP EPS of $1.09. Adjusted EPS was $1.10, beating the $1.04 consensus, and net income rose 20.4% to $68.3 million. The $0.37 common dividend used about 34% of GAAP EPS, and preferred holders get paid before common holders. Credit costs also fell: the provision for losses dropped to $3.3 million from $33.0 million after two problem loans were charged off.

Structure poses the biggest risk here. Because the preferred is non-cumulative, the board never makes up any missed payments. Revenue of $199.07 million also missed the $203.94 million estimate, and a CEO transition is set for year-end.

Union Bankshares (UNB): First to Pay of the Three

Union Bankshares, the Vermont parent of Union Bank, declared $0.36 per share on October 21. The ex-date is October 30, the record date is October 31, and the money arrives November 5, the earliest of the three. The $1.44 annual rate on a $23.04 share price yields 6.25%.

Coverage looks solid. Third-quarter GAAP EPS of $0.77 puts the quarterly payout ratio at 46.8%, and trailing EPS of $2.62 puts the annual payout ratio near 55%. Net income rose 9.7% to $3.77 million, net interest income grew 10.0%, and credit loss expense was just $34,000.

Some of that yield shows a stock that has gone nowhere. Shares are down 2.72% over one year and 8.71% over five years. Two things deserve attention: the accumulated unrealized securities loss grew to $40.7 million, and a $113.95 million market cap means trading can be thin.

Several other stocks also go ex on October 30.

Miss October 29 and You Miss This Payment

Buying a stock to catch one payment rarely pays off, because the share price usually falls by about the dividend once trading begins without it. Income investors typically consider whether they would want to own a stock after the cash arrives. Either way, the deadline is firm: anyone who isn’t a holder before October 30 won’t get the November payment.

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