Leaving employer coverage is the single most common reason people arrive here, and it is a transition with more moving parts than it looks.
First, which destination
Two different routes, decided mostly by age and eligibility.
If you are Medicare-eligible, losing employer coverage generally opens a Special Enrollment Period for Part B and for a drug plan. This is the route where the timing rules are strictest.
If you are not, the Marketplace is usually the destination, and losing job-based coverage is a qualifying event that opens a window there.
A household can need both at once — one spouse to Medicare, one to the Marketplace. That is normal and worth flagging early, because the two have different clocks.
The clock starts at the event
For both routes, the window generally runs from when coverage ends, not from when you started looking.
The sequence that goes wrong is always the same: coverage ends at month end, the person plans to “sort it out shortly”, and a meaningful part of the window is gone before they look properly.
If you know the date in advance — a retirement, a notice period — start four to six weeks before it, not after.
What COBRA does, and does not do
COBRA lets you continue the employer plan for a period, at your own cost.
Three things about it catch people:
It is generally not creditable coverage for delaying Part B. Relying on COBRA to postpone Medicare enrolment is one of the more expensive assumptions in this area. Assume it is not, and check.
Electing it can complicate the alternative. Taking COBRA and then changing your mind part-way through does not reliably re-open the window you passed up. Letting it run out on its own schedule generally does open one; dropping it voluntarily generally does not.
It is a decision with a deadline, made in a period when most people are dealing with other things.
If COBRA is in front of you now, that is worth a phone call before you elect or decline. Us, a Navigator, or 1-800-MEDICARE — all free.
The documentation
Both routes generally want proof that the coverage ended: a termination letter, a certificate of coverage, or a letter from the plan administrator.
Get it at the time. It is easy to obtain in the week you leave and difficult six months later, and coverage approved pending documents can be rescinded if they do not arrive.
The sequence that works
- Find the end date of the current coverage, precisely.
- Ask for the termination letter before you leave, not after.
- Decide the destination — Medicare, Marketplace, or one of each for a couple.
- Check networks and formularies against your actual doctors and prescriptions.
- Confirm the new start date in writing before anything is cancelled.
- Only then deal with COBRA or the old plan.
The gap nobody plans for
Even done correctly, there can be a short period between coverage ending and the new plan starting. Ask specifically what your effective date will be — it is a different question from “am I eligible” and the answer changes what you should do about care in the meantime.
If you have a procedure, a prescription refill or an appointment in that window, say so early. Sometimes the effective date can be arranged around it; sometimes it cannot, but knowing beforehand is always better.
Where to get this checked
We will walk it with you at no cost, for the plans we can offer. If your situation is simple, HealthCare.gov and the Medicare Plan Finder will get you the same answer free, and a SHIP counsellor or a Navigator will sit with you through it while selling nothing.
Where to check this independently
Nothing on this page is advice about your situation, and none of it replaces the free sources. The Medicare Plan Finder,1-800-MEDICARE, your SHIP counsellor andHealthCare.gov are free, independent, and show plans we cannot sell.
Healthbase is a licensed insurance agency, not a government agency and not connected with Medicare or any federal or state program.