Medicare Special Enrollment Period · Updated June 2026

Lost employer or union coverage? Your Medicare SEP (including COBRA)

A qualifying life event can open a Special Enrollment Period to change your Medicare coverage outside the normal windows. Here's exactly what applies when you lose job-based coverage.

By TemplateTitanHQ · ✓ Rules verified against CMS & Medicare.gov

Quick answer: If you leave coverage from an employer or union — including COBRA coverage — you can join a Medicare Advantage or Part D drug plan. Your chance to join lasts for 2 full months after the month your coverage ends.

Your Special Enrollment Period window
Your chance to join a Medicare Advantage plan or Medicare drug plan lasts for 2 full months after the month your employe
Triggered when you lose job-based coverage
Your chance to join a Medicare Advantage plan or Medicare drug plan lasts for 2 full months after the month your employer, union, or COBRA coverage ends.

What you can do during this Special Enrollment Period

Join a Medicare Advantage plan (with or without drug coverage) or a standalone Part D drug plan so you're not left without prescription coverage when your group plan ends.

When your new coverage starts

Coverage generally begins the first day of the month after the plan gets your request. Don't wait until the last week — line up the new plan before the old one stops.

Who this applies to

People who had health or drug coverage through their own or a spouse's employer or union, and people coming off COBRA. Note: for Part B itself, losing job-based coverage tied to current employment opens a separate 8-month Special Enrollment Period — but COBRA and retiree coverage do not count as current-employment coverage for Part B.

Not sure which window you're in?

Our free enrollment finder walks through your situation and points you to the right Medicare window — no signup, no email.

Open the Enrollment Finder →

Frequently asked questions

Does COBRA give me a Medicare Special Enrollment Period?

For Medicare Advantage and Part D drug plans, yes — leaving COBRA gives you 2 full months after the month it ends to join a plan. But COBRA does NOT count as current-employment coverage for Part B, so it will not extend or restart your Part B sign-up window. Many people should take Part B before COBRA ends to avoid a permanent Part B penalty.

How is this different from the 8-month Part B window?

Two different rules. This 2-month SEP is for joining a Medicare Advantage or drug plan. The 8-month Part B Special Enrollment Period is for enrolling in Part B itself and starts when your current-employment coverage (or the job) ends. See the late-penalty calculator for what missing the Part B window costs.

Related Medicare windows & tools

Moved
The SEP window when you move.
Moved back to the U.S.
The SEP window when you move back to the U.S..
All Medicare Enrollment Periods
IEP, AEP, OEP, GEP and every SEP in one place.
Late Penalty Calculator
What missing a window costs — permanently.

Medicare agent tracking client SEPs?

Special Enrollment Periods are short and event-driven — miss one and the client waits months. A dated SEP log is the difference between a saved client and a lost one. This page is free to share. The Medicare SEP Tracker gives you a ready-made spreadsheet to log every client's qualifying event and deadline so nothing slips.

See the Medicare SEP Tracker on Etsy →

Official sources

These windows are based on U.S. government Medicare enrollment rules: