Retirement timing and Medicare

6 months before retirement (any age)

Regardless of when you plan to retire, start your Medicare planning 6 months early:

• Contact Social Security to begin your Medicare enrollment
• Get Form CMS-L564 from your employer
• If you have an HSA, stop contributions 6 months before Part A starts
• Talk to a licensed Medicare agent to compare plans
• Review your employer's creditable coverage notice for Part D

Retiring at 66

If you delayed Medicare at 65 while working, you'll use your Part B Special Enrollment Period. You have 8 months from the date your employer coverage ends. Your Part B coverage starts the first day of the month after you enroll. Enroll in Part D within 2 months of losing employer drug coverage.

Retiring at 67

Same process as retiring at 66 — use your SEP. Two years of delayed Part B means no penalty as long as you had continuous employer coverage. If you enrolled in Part A at 65, you've been covered for hospital care the whole time.

Retiring at 68

Three years of employer coverage after 65. Your 8-month SEP still applies. At this point, also consider whether delaying Social Security benefits to 70 makes sense for your situation — Medicare and Social Security are separate decisions.

Retiring at 70

Maximum Social Security benefits kick in at 70. Five years of delayed Part B enrollment — no penalty with continuous employer coverage. Your 8-month SEP works the same way. Many people find that coordinating their Social Security start date with Medicare enrollment simplifies the transition.

The enrollment timeline

Timeline	Action
6 months before	Start Medicare planning, contact an agent
3 months before	Apply for Medicare at Social Security
Last day of work	8-month Part B SEP clock starts
Within 2 months	Enroll in Part D plan
Within 8 months	Complete Part B enrollment with Form CMS-L564
Within 6 months of Part B	Guaranteed Medigap enrollment (no health questions)