Derek Winbush is 63, lives in Boston, and has cirrhosis, kidney disease, nerve damage in his feet that makes walking difficult, vision problems, vertigo, and is HIV positive. He can't work steadily. He also doesn't qualify for a formal disability exemption under SSI or SSDI, which means when Medicaid work requirements take effect in Massachusetts, he'll be required to work, volunteer, or complete job training for 80 hours a month to keep his coverage.

He is, according to the Boston Globe's May 21 reporting, representative of a much larger population: approximately 300,000 MassHealth enrollees who have serious chronic health conditions that prevent them from meeting the 80-hour monthly requirement but who fall outside the federal definition of "disabled."

The federal law creating work requirements included a "medically frail" exemption specifically for people like Winbush. CMS is supposed to publish the final definition of that exemption on June 1. But even when it's published, it may not protect everyone in this gray zone.

What the Medically Frail Exemption Does and Doesn't Cover

The OBBBA legislation, the federal law that mandated Medicaid work requirements, includes five categories of people who may qualify as medically frail:

1. Blind or disabled per the Social Security Act (SSI/SSDI recipients)
2. Substance use disorder
3. Disabling mental illness
4. Physical, intellectual, or developmental disability that significantly impairs the ability to perform one or more activities of daily living
5. Serious or complex medical condition

The fifth category, "serious or complex medical condition," is the one that's supposed to catch people like Winbush. The problem is that CMS hasn't defined what qualifies. Is cirrhosis serious enough? Kidney disease? Vertigo that prevents steady employment? The June 1 guidance will answer that question, and the answer may be narrower than the plain language suggests.

States are already preparing for this ambiguity. MassHealth is building data connections to Department of Revenue wage data, plus five additional databases including the Department of Transitional Assistance, the VA, and the National Student Clearinghouse. It's also linking claims data to identify medical conditions that might meet the medically frail standard once CMS defines it.

Elizabeth LaMontagne, MassHealth's Chief Operating Officer, told the Globe that those datasets will be integrated before work requirements go live. That integration matters because it determines who gets flagged for an exemption and who gets a notice requiring 80 hours of work per month.

The database will sort you. You may not know the criteria it used.

When Work Requirements Take Effect

Work requirements don't apply to current Medicaid recipients until their next recertification after January 1, 2027. For most Massachusetts enrollees, that means coverage is protected through the end of 2026 and into early 2027 depending on when their annual review falls.

Nebraska started enforcement May 1. Montana and Iowa begin later this year. Arkansas is launching a soft start in July with penalties beginning in January 2027. Massachusetts is following the federal timeline, which gives families time to prepare but not unlimited time.

The state's budget proposal includes $30 million to preserve health care access during the transition and $6.2 million to hire approximately 70 new employees to handle exemption determinations, outreach, and compliance monitoring.

What to Do If You're in the Gray Zone

If you have serious chronic health conditions that prevent you from working 80 hours a month but you don't receive SSI or SSDI, you're in the gray zone. Here's what you can do now to protect your coverage before work requirements take effect.

1. Document Every Health Condition and Functional Limitation

Write down every diagnosed condition you have and every functional limitation it causes. Include:

• The diagnosis: cirrhosis, kidney disease, vertigo, or any other chronic condition
• How it limits your ability to work or perform daily activities
• Any medications you take and their side effects
• Frequency of medical appointments or treatments
• Any assistive devices you use: cane, walker, oxygen, or other equipment

Keep this list updated. You'll need it when you apply for a medically frail exemption.

2. Request a Written Statement from Your Doctor

Before June 1, ask your primary care physician or specialist to write a statement describing:

• Your diagnosed conditions
• How those conditions limit your ability to work or perform activities of daily living
• Whether you're capable of working 80 hours per month given your current health status

This isn't a formal disability determination. It's documentation that supports your medically frail exemption application when the time comes. Get it now, before the June 1 guidance is published and before the January 2027 recertification window starts.

3. Register for MassHealth Alerts

MassHealth will be running a required outreach campaign from June 30 through August 31, 2026. Register for email and SMS alerts now so you receive notices about exemption applications, recertification deadlines, and changes to the medically frail definition.

You can register through your MassHealth account online or by calling the MassHealth customer service line.

4. Track the June 1 CMS Guidance

CMS is publishing final guidance on the medically frail exemption on June 1. That guidance will define what qualifies as a "serious or complex medical condition." Read it when it's published. If your conditions don't fall within the definition, you'll know immediately that you need additional documentation or an appeal strategy.

The University of Michigan researcher quoted in the Globe report said it plainly: "Those most affected will likely be adults with significant health challenges who don't meet the formal disability criteria, exactly the population our research shows benefits most from coverage."

What States Are Doing to Prepare

Massachusetts is not the only state building database infrastructure to sort enrollees before work requirements take effect. Every state implementing work requirements is connecting wage data, benefit program enrollment, and medical claims to identify who qualifies for exemptions and who doesn't.

That sorting happens before you see a notice. By the time you receive a letter telling you to work 80 hours a month or lose coverage, the state has already determined you don't qualify for an exemption based on the data it has.

If that determination is wrong, if you have conditions that should qualify you as medically frail but the database didn't flag them, you'll need documentation ready to appeal. That's why requesting a written statement from your doctor now matters.

What Happens If You Lose Coverage

If you don't meet the 80-hour monthly requirement and you don't qualify for an exemption, MassHealth will terminate your coverage. You can reapply, but you'll need to show that you've come into compliance with the work requirement or that you now qualify for an exemption.

The gap between losing coverage and getting it back can be weeks or months depending on how quickly you can document your exemption or meet the work requirement. During that gap, you're uninsured.

For someone like Derek Winbush, who has cirrhosis, kidney disease, nerve damage, vision problems, vertigo, and HIV, losing Medicaid coverage isn't an administrative inconvenience. It's a health crisis.

The Hope and the Reality

Experts quoted in the Globe report said they hope CMS recognizes that states are facing an impossible deadline and will make it relatively easy to get exemptions, at least through 2027. The reality is that 300,000 Massachusetts enrollees are at risk, and the medically frail exemption may not protect all of them even after it's defined. The best protection is documentation: a written record of your conditions, your functional limitations, and your doctor's assessment of your ability to work.

Get that documentation now. Before June 1. Before your recertification notice arrives. Before the database makes a determination you'll have to appeal.