This printable checklist walks you through when to enroll, how to avoid late-enrollment penalties, what counts as creditable drug coverage, and key timing issues like HSA contributions and IRMAA reconsiderations.
Educational only—not tax or legal advice.
This printable checklist walks you through when to enroll, how to avoid late-enrollment penalties, what counts as creditable drug coverage, and key timing issues like HSA contributions and IRMAA reconsiderations.
Educational only—not tax or legal advice.
Instant download + email copy
Your 7-month Initial Enrollment Period window and when coverage starts based on sign-up timing.
Special Enrollment Period if working past 65—why COBRA doesn't extend your clock.
General Enrollment Period rules—coverage now starts the month after you sign up.
Part B (+10%/year) and Part D (+1%/month) penalties—and how to avoid them.
What qualifies as creditable drug coverage and why you need to keep the annual notice.
Income-related surcharges and how to request reconsideration after life-changing events.
Stop HSA contributions ~6 months before enrollment and watch for retroactive Part A.
A preview of what's covered in the checklist—step by step.
Map your IEP: It runs from 3 months before your 65th birth month through 3 months after. Coverage start depends on when you enroll—it always starts on the first of a month.
If you'll keep active employer coverage past 65 (you or spouse), confirm it's group health plan coverage and whether you can delay Part B without penalty.
HSA timing: Plan to stop contributions ~6 months before you apply for Medicare/SS benefits (Part A can be retroactive up to 6 months).
Decide whether to enroll in Part A & Part B now or delay Part B if you have qualifying active employer coverage.
If you don't have creditable drug coverage, enroll in Part D (or an MA plan with drug coverage) during IEP to avoid penalties. Keep any creditable-coverage letter from your plan.
Coverage start dates: Enroll before your birth month → coverage starts your birth month. Enroll during/after → coverage starts the next month.
When employment or employer coverage ends (whichever first), your SEP is 8 months to enroll in Part B without penalty—COBRA doesn't extend that window.
If you already have Part A, add Part B during SEP; then choose Part D or MA-PD (drug coverage timing has its own shorter window—don't let 63+ days elapse without creditable coverage).
Get the complete printable checklist
Download the ChecklistStandard monthly premium
Annual deductible
Maximum plan deductible
Out-of-pocket maximum
Single / Married filing jointly
Hospital deductible per benefit period
Seven months: 3 months before your 65th birth month through 3 months after. Coverage start dates depend on when you enroll and always begin on the first of a month. Enrolling before your birth month means coverage starts that month; enrolling later means it starts the following month.
No. Your 8-month Special Enrollment Period starts when employment or employer coverage ends—COBRA doesn't extend it. COBRA is considered continuation coverage, not active employer coverage, so it won't protect you from late enrollment penalties.
Part B: +10% for each full 12 months you went without Part B and didn't qualify for SEP. This penalty lasts as long as you have Part B. Part D: +1% per month without Part D or creditable drug coverage for 63+ days. In 2026, the penalty is calculated on $38.99/month.
Possibly. If retirement reduced your income, file Form SSA-44 to request an IRMAA reconsideration. Qualifying life-changing events include retirement, marriage, divorce, death of a spouse, work stoppage, or loss of income-producing property. You can submit SSA-44 online through your my Social Security account.
Plan to stop about 6 months before you apply for Medicare or Social Security benefits, since Part A can be retroactive up to 6 months. Contributing to an HSA while enrolled in any part of Medicare (including retroactive Part A) can result in tax penalties.
Our guides are a starting point. For personalized help coordinating Medicare enrollment with your retirement timing, HSA strategy, and income planning, schedule a 20-minute introductory call.
Or call us directly: (480) 597-1743
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