Written & Reviewed by
Last updated: May 27, 2026
Bottom line: If your retiree health plan, union plan, or COBRA coverage is ending, do not wait until the last week. The biggest danger is Medicare Part B. Medicare says the 8-month Part B Special Enrollment Period is tied to coverage from current work ending, not to retiree coverage or COBRA ending. Drug coverage has a different rule. A gap of 63 days or more without Medicare drug coverage or other creditable drug coverage can lead to a Part D penalty.
Emergency help now
- Find the true end date: Read the notice and write down the last day for medical coverage, drug coverage, dental, vision, and each family member.
- If you do not have Medicare Part B: Go to Social Security’s Part B page today. Ask whether you can use the Special Enrollment Period and what proof Social Security needs.
- If you have prescriptions: Ask the plan for written proof that your drug coverage is creditable through a certain date. Medicare’s creditable coverage rules are separate from Part B.
- If a spouse or dependent is covered: Ask whether that person has a separate COBRA right, Marketplace window, Medicaid path, or another employer plan option.
Quick help
- Do not cancel old coverage until the new start date is confirmed in writing.
- Do not assume COBRA lets you delay Part B.
- Call your local SHIP office for free Medicare counseling.
- Keep the older adult on the call if an adult child is helping, unless the plan already has permission to speak with the helper.
- Save the notice, the envelope, every bill, and every phone note.
Quick-reference table
| Situation | First step | Main warning |
|---|---|---|
| You are 65 or older and do not have Part B | Contact Social Security and ask about Part B enrollment. | COBRA and retiree coverage usually do not protect the Part B deadline. |
| You already have Parts A and B | Compare Original Medicare with Medigap and Part D, Medicare Advantage, and any new retiree option. | Doctor networks, drug lists, and Medigap rights can change the best choice. |
| Your drug coverage is ending | Ask for the last day of creditable drug coverage in writing. | A 63-day gap can create a lasting Part D penalty. |
| A spouse is under 65 | Compare COBRA, Marketplace coverage, Medicaid, and any spouse employer plan. | The spouse’s best path may be different from the retiree’s path. |
| The notice is unclear | Call the plan administrator and ask for written answers. | A plan switch and a plan termination are not the same thing. |
Contents
First decide what is ending
Start here: The label on the coverage controls the deadline. Ask if the ending coverage is active employee coverage, retiree coverage, COBRA, a union retiree plan, or a move into a new group Medicare plan.
Coverage from current work is different from coverage after work ends. Medicare’s working past 65 guidance says the 8-month Part B Special Enrollment Period starts when the work or the job-based coverage ends, whichever happens first. This is true even if you choose COBRA or another non-Medicare plan after that.
Retiree coverage is usually coverage from a former employer or union. Medicare’s retiree insurance page says Medicare generally pays first after you retire, and the retiree plan pays second. Some retiree plans may not pay much, or may not pay at all, if you were supposed to have Medicare and did not enroll.
COBRA is also not active employee coverage. Medicare’s COBRA guidance says COBRA does not give extra time to sign up for Part B. This is the rule that surprises many families.
Medicare Part B deadline
The main rule: If you delayed Part B because you or your spouse were still working, count from the date the work-based coverage ended or the work ended. Do not count from the date COBRA ends. Do not count from the date retiree coverage ends.
Part B helps cover doctor visits, outpatient care, medical equipment, preventive care, and many services outside the hospital. If you miss the Special Enrollment Period, Medicare’s coverage start page says you may have to use the General Enrollment Period from January 1 through March 31. Coverage starts the month after you sign up, and a late penalty may apply if you do not qualify for a Special Enrollment Period.
The penalty can last as long as you have Part B. That is why Part B should be handled before comparing every plan detail. A retiree plan ending notice may look like an insurance shopping problem, but for many seniors it is first a Medicare deadline problem.
If you already have Part A and need Part B, Social Security may ask for CMS-40B and CMS-L564, or other proof of employer coverage. Use the SSA Part B answer to check current online, fax, and mail options before sending forms.
| If you have | Part B risk | What to ask |
|---|---|---|
| Active employer coverage through current work | You may have a Special Enrollment Period when work or coverage ends. | What exact date did active coverage end? |
| Retiree coverage only | It usually does not extend the Part B window. | Did active coverage end months or years ago? |
| COBRA | It usually does not create a new Part B window. | When did the job or active coverage end? |
| Spouse’s current employer plan | It may protect you if the rules for current work coverage apply. | Is the spouse still actively working, and what is the employer size? |
Prescription drug coverage
Do not mix this up with Part B: Drug coverage has its own rule. A retiree or COBRA drug plan may still be useful if it is creditable. Creditable means the drug coverage is expected to pay, on average, at least as much as standard Medicare drug coverage.
CMS says plan sponsors must give creditable notices to Medicare-eligible retirees, COBRA enrollees, dependents, and others covered by the drug plan. Keep every notice. If the plan says the coverage is not creditable, or if the coverage ends, act quickly.
Medicare’s plan enrollment page lists special windows for people who leave employer or union coverage, including COBRA coverage, or lose creditable drug coverage. The timing depends on your facts, so ask the plan for the exact last day of drug coverage and the exact last day it is creditable.
For deeper help with drug costs, see our prescription cost help guide. If the problem is choosing cheaper medicines, coupons, or pharmacy assistance, our prescription assistance guide may also help.
COBRA and family members
COBRA can help some families: It may be a bridge for a younger spouse, a dependent child, or a person who needs to keep the same doctors for a short time. It is not usually a good reason for a Medicare-eligible retiree to delay Part B.
The Department of Labor’s COBRA worker FAQs say you generally have 60 days to elect COBRA, starting from the later of the coverage loss date or the date the election notice is provided or mailed. If you elect COBRA, you then have 45 days to make the first payment.
COBRA can also be expensive. The Department of Labor’s COBRA overview says you usually pay the full premium unless the employer helps. Federal COBRA generally applies to covered employers with 20 or more employees. Some states have mini-COBRA rules for smaller employers, so ask your state insurance department if the employer is small.
A spouse or dependent may have a different path than the retiree. If the spouse is under 65, HealthCare.gov’s coverage loss page says loss of job-based coverage can open a Marketplace Special Enrollment Period. But HealthCare.gov also warns that Medicare and Marketplace coverage do not work together the same way. Its Medicare Marketplace page says people with Medicare generally do not need Marketplace coverage.
Choosing replacement coverage
Do this after Part B is handled: If you have Part A and Part B, the next question is how to cover gaps, doctors, drugs, and costs.
| Option | What it may help with | Reality check |
|---|---|---|
| Original Medicare plus Medigap and Part D | Broad doctor choice, help with Medicare cost-sharing, and separate drug coverage. | Medigap rights can be time-limited, and prices vary by state and company. |
| Medicare Advantage | One plan for Medicare benefits, often with drug coverage and extra benefits. | Check doctor networks, hospital networks, referrals, prior authorization, and drug lists. |
| New retiree or union option | May keep a subsidized plan that works with Medicare. | Joining a separate Part D or Medicare Advantage plan can affect some retiree benefits. |
| COBRA | May help a spouse or dependent keep coverage for a short time. | It can cost the full premium and does not fix a Part B delay. |
| Marketplace or Medicaid | May help a family member under 65 or a person who is not Medicare-eligible. | Marketplace rules are different once Medicare starts. |
Medicare’s buying Medigap page explains that after your Medigap open enrollment period ends, companies may not have to sell you a policy unless you have a guaranteed issue right. Ask SHIP or your state insurance department whether the end of employer or union coverage gives you a Medigap protection in your case.
If you are comparing employer coverage against Medicare, our Medicare versus private insurance guide can help you frame the choice. If your income is low and you may qualify for both Medicare and Medicaid, our dual eligible guide explains how the two programs can work together.
How to start without wasting time
Read the notice like a deadline letter
Circle the end date. Then underline every sentence about Medicare, COBRA, creditable drug coverage, dependents, appeals, and automatic enrollment into a new plan. If the notice says you will be moved into another plan, ask whether you can opt out and what happens if you do nothing.
Make one call to the plan administrator
Ask for the exact last day of medical coverage and drug coverage. Ask whether the drug coverage is creditable. Ask whether a spouse or dependent has a separate election right. Ask for all answers in writing.
Make one call to Social Security if Part B is missing
Tell Social Security the date active work coverage ended. Do not only say, “my retiree plan is ending.” That may hide the important date. If the active coverage ended long ago, ask what your next enrollment path is and whether any special rule may apply.
Check doctors and prescriptions before choosing a plan
For Medicare Advantage, check every doctor, hospital, drug, pharmacy, and prior authorization rule. For Original Medicare with Medigap, ask the insurer when the Medigap policy can start and whether medical underwriting applies.
Documents to gather
- ☐ The plan termination or change notice, plus the envelope if mailed
- ☐ Medical, drug, dental, and vision insurance cards
- ☐ Medicare card, if already enrolled
- ☐ COBRA election packet and premium bill, if received
- ☐ Notice of Creditable Coverage for prescription drugs
- ☐ Summary Plan Description and Evidence of Coverage
- ☐ List of doctors, hospitals, pharmacies, and prescriptions
- ☐ Recent Explanation of Benefits statements
- ☐ CMS-40B, CMS-L564, fax proof, and mail proof if applying for Part B
- ☐ Names, birth dates, and Medicare status for spouse and dependents
- ☐ Income papers if applying for Medicaid, Extra Help, or a Medicare Savings Program
Phone scripts
Plan administrator script: “My retiree health plan notice says coverage is changing. Please tell me the exact last day of medical coverage, the exact last day of drug coverage, whether the drug coverage is creditable, whether COBRA or another continuation option is offered, and whether my spouse or dependents have separate rights. Please send the answers in writing.”
Social Security script: “I have Medicare Part A and may need Part B. My active employer coverage ended on [date]. My retiree or COBRA coverage is ending on [date]. Am I still within a Part B Special Enrollment Period? What forms and proof do you need?”
SHIP script: “I need help comparing my options because my retiree plan is ending. I have [Part A only / Parts A and B]. My drug coverage ends on [date]. Can you help me compare Part B timing, Part D, Medigap, Medicare Advantage, and any state rules?”
Doctor office script: “My insurance is changing. Before I choose a new plan, can you tell me which Medicare Advantage plans you accept, whether you accept Original Medicare, and whether you are taking new patients under those plans?”
What to do if delayed, denied, or overwhelmed
If no COBRA packet arrived
Call the employer benefits office and the COBRA administrator. Ask when the qualifying event was recorded, when the election notice was mailed, and which address was used. Write down the name, phone number, date, and answer.
If the employer is slow with Part B proof
Start the Part B process anyway. Ask Social Security what substitute proof may be accepted. Old insurance cards, employer letters, pay stubs showing coverage deductions, and retirement paperwork may help show the dates.
If claims are billed wrong
Ask the provider to rebill after confirming which plan is primary and which is secondary. Medicare’s who pays first page explains primary and secondary payer rules. For coordination problems, Medicare’s coordination page lists the Benefits Coordination & Recovery Center number.
If you get a Part D penalty notice
Ask the former employer or union for written proof of creditable coverage and the exact ending date. Follow the plan’s reconsideration or appeal instructions. Include copies, not originals, unless the agency asks for originals.
Backup help for costs
Do not stop at insurance shopping: A retiree plan ending can expose other money problems. If premiums, deductibles, food, rent, or utility bills are now too high, check benefit programs too.
- Medicare costs: Medicare’s Savings Programs page explains state help with some Medicare costs. Our Medicaid for seniors guide can help you understand where Medicaid fits.
- Drug costs: Social Security’s Extra Help page explains help with Part D costs for people with limited income and resources.
- Social Security paperwork: Our Social Security guide can help if address, direct deposit, or benefit records need to be fixed during the change.
- Care while coverage changes: Our community health centers guide may help if you need a clinic that works with low-income patients.
- Household bills: Our help with bills and senior food programs guides cover other supports that may free up money for health costs.
- Housing pressure: If health premiums make rent harder to pay, our housing and rent help guide may point you to the right starting place.
Official help
- Medicare: 1-800-MEDICARE, or 1-800-633-4227. TTY users can call 1-877-486-2048. Medicare’s talk to someone page also lists live chat.
- Social Security: 1-800-772-1213. TTY users can call 1-800-325-0778. Use Social Security for Part B enrollment questions.
- SHIP: Use the SHIP locator for local Medicare counseling. SHIP is free and is not an insurance company.
- Employer or union plan: Use the benefits office, plan administrator, or COBRA administrator named in your notice.
- Marketplace: HealthCare.gov is mainly for people who are not Medicare-eligible, such as a younger spouse or dependent.
Reality checks
- Phone answers can be wrong: Ask for the answer in writing or by secure message.
- COBRA can be retroactive: That can help avoid a gap, but only if you elect and pay on time.
- Doctors can change networks: Check with the doctor’s billing office and the plan before enrolling.
- Drug formularies change: A plan that covers one medicine may not cover another, or may require prior approval.
- Spouses need their own plan: A younger spouse may need COBRA or Marketplace coverage even if the retiree moves to Medicare.
- Medigap rules vary: Federal rights are limited, and some states add extra rights.
Common mistakes to avoid
- Waiting for COBRA to end before checking Part B.
- Assuming retiree coverage is the same as active employer coverage.
- Throwing away the creditable drug coverage notice.
- Joining Part D without asking whether it affects retiree benefits.
- Canceling a retiree plan before the new plan is active.
- Ignoring the spouse or dependent’s separate coverage deadline.
- Choosing a plan before checking doctors, hospitals, drugs, and pharmacies.
- Relying on one phone call without keeping notes.
Resumen en español
Si su plan de salud de jubilado termina, no espere hasta el final de COBRA para revisar Medicare Parte B. Para muchas personas, el plazo especial de 8 meses para la Parte B empieza cuando termina el trabajo o la cobertura por empleo activo, no cuando termina COBRA ni el plan de jubilado.
La cobertura de medicinas tiene otra regla. Pida una carta que diga si la cobertura de recetas es acreditable y hasta qué fecha. Una brecha de 63 días o más sin cobertura acreditable puede causar una penalidad de la Parte D.
Si un cónyuge o dependiente es menor de 65 años, esa persona puede necesitar COBRA, un plan del Mercado, Medicaid, o cobertura por otro empleo. Llame a SHIP para ayuda local gratis, a Seguro Social para la Parte B, y a Medicare si hay dudas sobre quién paga primero.
FAQ
Does losing retiree coverage give me a Part B Special Enrollment Period?
Usually no. The Part B Special Enrollment Period is generally tied to coverage based on current employment ending, not retiree coverage ending. Ask Social Security if your facts are unusual.
Can COBRA let me delay Medicare Part B?
No. COBRA usually does not give extra time for Part B. It may help as temporary coverage, but it does not restart the Part B clock.
Can retiree or COBRA drug coverage protect me from a Part D penalty?
Yes, if the drug coverage is creditable. Keep written proof. When that coverage ends or is no longer creditable, act before a long gap starts.
What if I already have Medicare Parts A and B?
Then the main issue is replacement coverage. Compare any new retiree option, Original Medicare with Medigap and Part D, and Medicare Advantage.
What if my spouse is younger than 65?
Your spouse may need a different plan, such as COBRA, Marketplace coverage, Medicaid, or coverage from another employer. Ask about separate rights and deadlines.
What if I already missed the 8-month Part B window?
Contact Social Security and SHIP right away. You may need the General Enrollment Period, and a penalty may apply. Ask if any special rule fits your case.
Should I cancel old coverage once I pick a new plan?
Not until the new plan confirms the start date. If possible, get the start date in writing before canceling anything.
Can I use Marketplace coverage instead of Medicare?
Do not count on it. Once Medicare applies, Marketplace rules change. Under-65 family members may still be able to use the Marketplace.
About This Guide
This guide uses official federal, state, local, and other high-trust nonprofit and community sources mentioned in the article.
Editorial note: This guide is produced based on our Editorial Standards using official and other high-trust sources, regularly updated and monitored, but not affiliated with any government agency and not a substitute for official agency guidance. Individual eligibility outcomes cannot be guaranteed.
Verification: Last verified May 27, 2026, next review August 27, 2026.
Corrections: Please note that despite our careful verification process, errors may still occur. Email info@grantsforseniors.org with corrections and we will respond within 72 hours.
Disclaimer: This article is for informational purposes only and is not legal, financial, medical, tax, disability-rights, immigration, or government-agency advice. Program rules, policies, and availability can change. Readers should confirm current details directly with the official program before acting.
Last updated: May 27, 2026
Next review date: August 27, 2026
About the Authors