While most retirees are grateful to have their Social Security checks, many often feel they’re not enough. It would be great to have more than one monthly benefit coming in, though that’s not possible for most people.

A small group of seniors does get multiple checks each month, though. This month, they’ll actually receive three. There’s a chance you may even be able to join them if you meet certain criteria.

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How the Social Security Administration pays out benefits

The Social Security Administration has a very strict payment schedule. Most beneficiaries receive their payments on either the second, third, or fourth Wednesday of each month, which depends on your birthdate. It breaks down like this:

• Born on the 1st through the 10th: Second Wednesday of each month
• Born on the 11th through the 20th: Third Wednesday of each month
• Born on the 21st through the 31st: Fourth Wednesday of each month

This month, that corresponds to May 14, May 21, and May 28, respectively. But there’s a separate payment date for those on Supplemental Security Income (SSI).

SSI is available to low-income seniors, as well as people who are blind and disabled of any age. It’s an additional monthly benefit administered by the Social Security Administration. Its value varies depending on the state you live in and your income and assets. The federal maximum in 2025 is $967 per month for an individual or $1,450 per month for a couple.

The Social Security Administration typically pays out SSI benefits on the first of the month. But if the first falls on a weekend or a holiday, it pays out benefits on the last business day before the weekend or holiday. That’s what’s happening this month.

May SSI payments will go out on May 1 as scheduled. But June 1 is a Sunday. So the Social Security Administration will pay out June SSI benefits on May 30. So you’re not actually getting more money than you normally would. You’re just getting your June payment a little in advance.

Is SSI an option for you?

If your Social Security benefits don’t go far enough and you have little to no personal savings to supplement them, you may want to consider applying for SSI. You might be able to do this online if you’re applying for Social Security disability benefits at the same time. If you’re not, you might have to call the Social Security Administration or schedule an appointment at a field office.

Before you do that, it’s worth reviewing the SSI eligibility criteria. If you earn less than $2,019 per month from work and have resources — money in bank accounts, cars, etc. — of $2,000 or less for an individual or $3,000 or less for couples, there’s a good chance you’ll qualify.

You’ll need to provide details of your income and assets to qualify. This process may take some time. So even if you are eligible, you likely won’t be able to take advantage of the two SSI checks coming this month. However, signing up may improve your future finances.

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