6 High-Yield Dividend Stocks With Ex-Dates Days Away: Act Now or Miss the Payment

Oxford Square Capital (NASDAQ:OXSQ) pays $0.035 a month. At its $1.34 share price, that works out to an annualized yield of about 31.3%. The stock goes ex-dividend on Friday, October 16, the same day as one other high yielder on this list. Three more go ex on Monday, October 19. Investors have between one and two trading days to qualify, and in some cases the yield is high because the payout is exceeding earnings.

How the timing works: you must own the shares before the ex-dividend date to collect the payment. The pay date is simply when the cash shows up. If you buy on or after the ex-date, you miss that payment.

Horizon Technology Finance (HRZN): 23.6% Yield, Ex-Dividend October 16

Horizon Technology Finance (NASDAQ:HRZN) goes ex-dividend on October 16, 2026, so today, October 15, is the last day to buy. The monthly distribution is $0.09, payable November 16, and is made up of a $0.06 regular payment plus a $0.03 special. At $4.57, the full payout yields about 23.6%. The regular portion alone yields about 15.8%.

For a BDC (business development company), the right measure is net investment income (NII). Second-quarter NII came in at $0.11 per share, missing the $0.1126 consensus. One-time merger expenses of $4.44 million cut NII by about $0.07 per share. Without those costs, NII covered the regular distribution, but the special payment sits on top of that coverage.

Net asset value (NAV) per share fell to $6.23 from $6.98 at the start of the year. Five loans carry the lowest credit rating, with a fair value of $31.3 million against a cost of $58 million. The stock is down 17.32% year to date, so part of the yield comes from a falling price.

Oxford Square Capital (OXSQ): 31.3% Yield With Thin Coverage

Oxford Square also goes ex on October 16, which makes today the last day to qualify. Shareholders will receive $0.035, payable October 30. The payout has held at that level every month since at least January 2025.

Coverage is the problem. Second-quarter earnings were $0.05 per share, against three monthly payments that add up to $0.105. Total NII slipped to $5.14 million from $5.50 million a year earlier. Over the same period, NAV per share dropped to $1.29 from $2.06. Part of the pressure came from roughly 11.3 million new shares sold through an at-the-market program, and net realized losses added about $5.2 million. A yield above 30% combined with a shrinking NAV is a warning sign, and it is one of several we catalogued in a free report on the seven tells that a big payout is about to be cut.

Seven Hills Realty Trust (SEVN): 16.0% Yield, Ex-Dividend October 19

Seven Hills Realty Trust (NASDAQ:SEVN) goes ex-dividend on October 19, making Friday, October 16, the final day to purchase shares. The quarterly dividend is $0.28, payable November 12, which works out to about 16.0% at $6.98.

For a mortgage REIT, distributable earnings are the measure that matters. Second-quarter distributable earnings were $0.23 per share, short of the $0.28 payout, for a payout ratio of roughly 122%. A $4.92 million credit-loss provision drove GAAP results to a loss. Management says it is on plan to cover the dividend by year end.

All loans in the portfolio are fully performing, and the company holds $70 million in cash. Shares are down 22.69% over the past year, which has drove the yield higher. Book value is $14.15 per share.

Industrial Logistics Properties Trust (ILPT): 5.8% Yield With the Strongest Coverage

Industrial Logistics Properties Trust (NASDAQ:ILPT) goes ex on October 19, with the $0.10 quarterly dividend payable November 12. The last day to buy is October 16. At $6.86, the yield is about 5.8%.

Second-quarter Normalized FFO (funds from operations, the standard REIT cash earnings measure) was $0.31 per share, or 3.1 times the dividend. Full-year guidance of $1.31 to $1.39 is well above the $0.40 annualized payout. Occupancy rose to 99.1%. The weak spot is the balance sheet: net debt runs at 11.5x adjusted EBITDAre, and a single tenant accounts for 27.7% of rents. The yield is low because the stock is up 27.44% this year. For context, ILPT paid $0.33 a quarter in 2021.

RMR Group (RMR): 9.9% Yield That Depends on Incentive Fees

RMR Group (NASDAQ:RMR), which manages both ILPT and Seven Hills, shares their October 19 ex-date. The $0.45 quarterly dividend is payable November 12, and the last day to buy is October 16. At $18.13, it yields about 9.9%.

RMR is a regular corporation, so EPS is the right test. Fiscal second-quarter adjusted EPS was $0.11, meaning the dividend ran at about 409% of earnings in that quarter. Fee-paying assets under management fell to $37.1 billion from $39.8 billion. Coverage depends on incentive fees. RMR collected $23.6 million of these fees for 2025, and management says its managed REITs, including ILPT, are on pace to generate nearly $33 million for 2026. The dividend has held at $0.45 since 2024, and the stock is up 31.55% year to date.

Deadlines That Decide Who Gets Paid

Note that shares must be owned before today’s close to capture the October 16 payments from Horizon and Oxford Square. For Seven Hills, ILPT and RMR, Friday is the deadline. Missing the ex-date means missing the payment. Chasing a single dividend is a weak income strategy, though, because the share price typically falls by roughly the dividend amount on the ex-date. Coverage counts for more than the yield, and on that measure ILPT is the only name here making well more than it pays out.

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