Retiring after 65
Leaving employer coverage after 65
Figures on this page checked . Medicare and marketplace numbers reset every year — if you are reading this long after that date, call and we will tell you what moved.
The eight-month clock, and the day it starts
Leaving a job with group health coverage opens a Special Enrollment Period of 8 months to sign up for Part B with no late penalty. That much most people know.
The day it starts is the part that costs money
The eight months begin when your employment ends or when the group plan ends, whichever happens first. Not when COBRA runs out. Not when retiree coverage ends. If your last day was in March and you elected COBRA through the following February, your window closed in November while you were still covered.
We meet people in month ten of exactly that story. By then the only door left is the General Enrollment Period, coverage starts the month after they enroll, and Part B costs 10% of the standard premium for each full 12 months they could have had it and did not — for as long as they have it.
So the first date to write down is not your retirement date. It is the last day your group plan pays as a plan you hold through current employment.
Two forms, and your employer signs one of them
Enrolling through this window differs from enrolling normally, because Social Security needs proof you were covered. That proof is the second form, and it is the one that depends on somebody else’s calendar.
- CMS-40B — Application for Enrollment in Medicare Part B. Yours to complete. This is the actual request for Part B.
- CMS-L564 — Request for Employment Information. Your employer or the plan administrator completes and signs this, confirming the dates you were covered through current employment.
Both go to Social Security together. Start the second one early. You are asking a human resources department to find records for somebody who no longer works there, and two weeks of silence in month seven is a bad place to be standing.
In plain terms
“The employer never sent it back” is a situation Social Security has seen before. Bring what you do have: pay stubs showing premium deductions, insurance cards with dates, plan documents. Ask them what else will serve. Do not miss the deadline waiting for a form.
COBRA is not a bridge to Medicare
COBRA feels like continued employer coverage. For Medicare purposes it is not, because it does not come from current employment, and that distinction is what the eight-month rule turns on.
Two separate problems follow. Your Part B window keeps running while you are on COBRA, as above. And once you are entitled to Medicare, COBRA generally pays second — so a plan you are paying full price for can end up covering almost nothing, because it expects a Medicare you never enrolled in to have paid first.
Some situations still make COBRA the right choice: a course of treatment underway with a specific provider, a spouse or child under 65 who needs the coverage to continue, a deductible already met for the year. Those are real reasons and we will help you weigh them. Do not let COBRA set your Part B timing.
Your prescription coverage has its own deadline
Part B is not the only clock running. When employer drug coverage ends, you need Part D coverage in place before long, and the line is specific.
The 63-day line
Go 63 continuous days or longer without creditable drug coverage after your Part D enrollment period has ended, and a late enrollment penalty attaches. Like the Part B penalty, it is permanent.
In plain terms
“Creditable” means your employer’s drug coverage is at least as good as Medicare’s, on average. Your plan has to tell you in writing each year whether it is. Find that letter before you leave, and keep it — it is what proves you owe no penalty.
Retiree drug coverage is sometimes creditable and sometimes not, and people assume rather than check. One phone call to the plan settles it, and the answer decides whether you need a Part D plan the month you retire or not at all.
What opens the day Part B starts
This is the piece that makes retirement a better moment than people expect. Your Medigap Open Enrollment Period — 6 months during which no carrier can ask you a health question — starts the first day you are both 65 or older and enrolled in Part B.
Delay Part B until 68 because you were working, and that window has been waiting for you. It opens now, not three years ago. Nothing was lost by working, and this is the one moment when a Medicare Supplement policy is available to you whatever your health history.
After it closes, Colorado carriers may medically underwrite. No birthday rule and no annual do-over exists in this state, whatever a search result written for California tells you.
Five steps, and the order matters
- Three months before your last day: ask human resources for the CMS-L564 and ask whether your drug coverage is creditable. Both requests, one email.
- If you have a health savings account: stop contributing six months before you apply. Part A backdates, and the tax consequence is real.
- Submit both forms to Social Security once you have a firm end date. Early in the window, not late.
- Choose Medigap or Advantage before Part B starts, so coverage is continuous and your six-month window is not spent deciding.
- Check your prescriptions against the plan you pick. Every year after this one, too.
Tell us your last day and your employer size and we will put dates on all five. It takes about half an hour.
Questions about retiring after 65
My last day is in June but my coverage runs to July 31. When does my window start?
Most likely August 1, because employers commonly run group coverage to the end of the month and it stays coverage through current employment until then.
The rule is that the clock starts when employment ends or when the group plan ends, whichever comes first — so the answer turns on what your employer does after your last day. Ask them to put the coverage end date in writing, then call us with it. Guessing at this one is how people lose the window.
Can I take COBRA and sort out Medicare later?
You can take COBRA, but it does not pause your Medicare deadline. Your eight-month Part B window started when the job or the group plan ended, and it keeps running the whole time you are on COBRA.
A second problem follows. Once you are entitled to Medicare, COBRA generally pays second, so you can be paying full price for a plan that only covers what Medicare would have left behind — while not being enrolled in Medicare at all.
What if my former employer will not complete the CMS-L564?
Tell Social Security. They have a process for it and they accept other evidence: pay stubs showing health premium deductions, insurance cards with coverage dates, plan documents, W-2s showing employer contributions.
Do not let the deadline pass while you wait. Submit your CMS-40B on time with whatever proof you have and explain the situation. A late application with a perfect form is worse than an on-time application with an imperfect one.
My spouse still works and I am on their plan. Does anything change for me?
Not yet. Coverage through a spouse’s current employment counts the same as your own, so you can keep delaying Part B while that job and that plan continue and the employer has twenty or more employees.
Your eight months will start when their employment or that plan ends. It is their retirement date that starts your clock, which is a detail couples routinely miss because they are each planning around a different calendar.
CMS-required disclaimer
We do not offer every plan available in your area. Currently we represent 7 organizations which offer 45 products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program to get information on all of your options.