The next four weeks could impact your benefits

If you’re enrolled in Medicare or planning to enroll soon, several key deadlines are approaching between now and mid-June. Missing them could lead to higher premiums, delayed coverage, or lost benefits. Here’s what you need to know—and how to act in time.
May 31: Last day for Part B Special Enrollment Period
If your job-based insurance recently ended, you may qualify for a Special Enrollment Period to sign up for Medicare Part B. That window closes on May 31 for those who lost coverage in March. Failing to enroll in time could result in permanent late penalties and a gap in outpatient coverage.
Ongoing: Medicare Advantage Special Enrollment
Special enrollment for Medicare Advantage plans is open for individuals who:
- Recently moved
- Lost Medicaid eligibility
- Experienced plan errors or dropped coverage
These windows typically last 60 days from the qualifying event. If you experienced any of these changes in April, your deadline could fall before June 15, so act now to avoid missing it.
June 15: Appeal deadline for May coverage denials
If Medicare denied a claim or prior authorization in May, you typically have 60 days to file an appeal. That means June 15 is the cutoff to challenge early-May denials for services like hospital stays, procedures, or prescriptions. Late appeals are often rejected, so don’t delay.
Working past 65? Know the HSA and Part A rules
Many people continue working past age 65 and delay Medicare enrollment. But enrolling in any part of Medicare, including Part A, makes you ineligible to contribute to a Health Savings Account (HSA). If you plan to sign up this spring or summer, talk to your HR department or tax advisor first.
Where to get help
If you’re unsure about deadlines or next steps, call 1-800-MEDICARE or visit Medicare.gov. You can also contact your local State Health Insurance Assistance Program (SHIP) for free one-on-one help. These counselors can walk you through enrollment, appeals, and plan choices.
Bottom line: Take action before it’s too late
From enrollment deadlines to appeal windows, the next four weeks are critical for many Medicare users. Make sure you know your dates, get your paperwork ready, and avoid the financial consequences of missing an important cutoff.