The short answer
When you leave job-based coverage before 65, a few clocks start at once. You can pick a Marketplace plan from 60 days before to 60 days after you lose that coverage. You have 60 days to elect COBRA, and it lasts up to 18 months after leaving a job. Open enrollment for 2027 runs November 1, 2026 to January 15, 2027. Medicare's first sign-up window is 7 months around the month you turn 65. The tool below puts your own dates on each one.
The dates, and where each one comes from
The tool does the arithmetic. Here are the rules it uses, so you can check any of them yourself.
1. The Marketplace window when work coverage ends
Losing job-based coverage opens a special enrollment period. HealthCare.gov says you can apply any time from 60 days before to 60 days after your separation date. That means you can compare plans and pick one before your last day instead of waiting until after.
2. The COBRA deadline
The Department of Labor gives you 60 days to enroll in COBRA, starting from when your coverage ends or when your election notice is provided to you, whichever is later. After you elect, you have 45 days to make the first payment. The tool shows the earliest that 60-day deadline can be. A late notice pushes it later.
3. How long COBRA lasts
For leaving a job, COBRA lasts up to 18 months. The tool counts 18 months from the day after your work coverage ends and tells you whether that reaches the month you turn 65. One catch: HealthCare.gov says you can't drop COBRA outside open enrollment and switch to a Marketplace plan. The window only opens when COBRA runs out, and then you have 60 days.
4. Open enrollment for 2027
Open enrollment runs November 1, 2026 to January 15, 2027. Enroll by December 15 for coverage that starts January 1. Enroll from December 16 through January 15 and coverage starts February 1. States that run their own marketplace can set different dates.
5. Medicare's first sign-up window
Medicare.gov describes the Initial Enrollment Period as 7 months long: it starts 3 months before the month you turn 65 and ends 3 months after it. Coverage always starts on the first of a month. If you sign up before your birthday month, it usually starts the month you turn 65. If your birthday is on the 1st, coverage starts the month before.
I don't sell Medicare. The tool shows the window so you can plan the years before it. When you get close, I can point you to someone I trust who does.
6. Your gap
The gap is the time between the day after your work coverage ends and the month Medicare usually starts. That stretch needs a plan of your own: COBRA, a Marketplace plan, or a private-market plan. Many private-market plans aren't ACA plans, and approval for those comes from health questions. The tool counts the months, which is the number every comparison starts from.
If your spouse is younger
Your move to Medicare doesn't move a younger spouse with you. They usually need their own coverage until they reach Medicare age too. When you switch, HealthCare.gov says to confirm the plan for others in your household who need to keep their Marketplace coverage.
About these dates
These are estimates worked out from the official rules linked on this page. Your plan's notices and your state's marketplace can set different dates, so confirm the ones that matter before you count on them. This page doesn't quote prices or decide what you qualify for.
Talk through your timeline with Ryan
Bring your dates and the doctors you want to keep. I'll show you what each option looks like for your gap.
Book a timeWant the longer version? Read retiring before 65 for what the gap costs and how income changes it, or COBRA vs. the marketplace if you already have the COBRA letter in hand.
Common questions
Can I pick a Marketplace plan before my job coverage ends?
Yes. HealthCare.gov says you can apply any time from 60 days before to 60 days after your separation date, so you can line up a plan before your last day.
If I take COBRA, can I switch to the Marketplace later?
Not whenever you like. HealthCare.gov says you can't drop COBRA outside open enrollment and enroll in a Marketplace plan instead. When COBRA runs out, you have 60 days to pick a Marketplace plan.
Does Caprio Health help with Medicare?
I don't sell Medicare. This tool shows your Medicare sign-up window so you can plan the years before it. When you get close, I can point you to someone I trust who does.