I'm over 65, not enrolled in Part A or B, and leaving active coverage through an employer with 20+ employees for six months of COBRA.

Question

Trever Dahms · Accepted Answer

No, once your active employer coverage ends, your 8-month Special Enrollment Period starts immediately, and COBRA doesn't extend or pause it. So even if you elect 6 months of COBRA, you still need to enroll in Part A and B within 8 months of your active coverage ending, not 8 months from when COBRA runs out. Waiting until COBRA ends would put you outside the SEP window and risk a late enrollment penalty plus a potential gap in coverage.

Answered by Trever Dahms on June 30, 2026

Broker Licensed in FL, NC, SC & WI

Answered by Trever Dahms Medicare Insurance Agent

Voss Speros · Answer

Voss Speros here. Greek god of Medicare. Medicare is all Greek to you, you're in luck, I'm Greek.

So the question, it's a long one so bear with me. I'm over 65, enrolled in my creditable coverage, never went on A and B. Okay. I'm going to retire, and instead of going on Medicare right away I'm going to roll onto COBRA for six months. Can I still enroll in Medicare because I'm still within the eight month time frame after COBRA, the eight month time frame? Okay, there's a long question.

So yes. If you're retiring and you're going to lose one, COBRA for six months, you have eight months from your retire date, from the date you lose your creditable coverage, to get on Medicare. Now if you spend six months of it on COBRA, you got two months left. You got to move quick, because if you miss the time then you got to wait till the general election period, and that's January 1st to March 31st.

So you might want to just look at going on Medicare right out the gate. But maybe there's a cost difference, I don't know. Maybe there's something with your benefits from work, maybe you have to go on COBRA, I don't know. But yes, you're going to COBRA for six months, there's still two months left over at the end. Just don't dilly dally around when you're getting close to that six month. Then start looking into it that fifth month, looking into it, because you can apply for Medicare and that's going to take some time. It takes about a month to apply for A and B and have it go into place, and then you got to get your other plans. So you don't want to miss any dates.

And I hope that helps. Give us a call if you have any other questions.

Robin Dall · Answer

Yes, if COBRA only lasts six months and you enroll in Medicare before the eight-month Special Enrollment Period runs out, you may be able to avoid the Part B late enrollment penalty. But COBRA does not extend that window. The eight months are counted from when active employment or active employer coverage ended — not from when COBRA ends.

Answered by Robin Dall on June 30, 2026

Broker Licensed in FL, AZ, KS & MO, NC, OH & TX

Answered by Robin Dall Medicare Insurance Agent

Kristina Guerry · Answer

Yes, you have an 8-month Special Enrollment Period to enroll in Medicare but it is not based off of COBRA. It is based off when your employer coverage ends. COBRA is only creditable for delaying your Medicare Part D plan. That is, as long as the COBRA is considered creditable coverage for Part D. I would recommend having a conversation with a broker one to two months prior to your employer coverage ending to have a plan and confirm that you understand everything.

Answered by Kristina Guerry on June 30, 2026

Broker Licensed in SC, AL, AR & 45 other states

Answered by Kristina Guerry Medicare Insurance Agent

Veronica Giron · Answer

Leaving employer coverage with 20+ employees qualifies you for an 8-month SEP to enroll in Medicare parts A & B. Cobra does not extend or restart the 8-month SEP, the clock starts when the employer coverage ends.

Answered by Veronica Giron on June 30, 2026

Broker Licensed in CO, AZ, CA & 8 other states

Answered by Veronica Giron Medicare Insurance Agent

Patricia Lewis · Answer

The question for today is: I'm over 65, not enrolled in Part A or B, and leaving active coverage through an employer with 20 plus employees for six months of COBRA. Can I enroll in Medicare if I'm still within the eight month period from which my active coverage ended?

The answer to that question is yes. You may still enroll in Medicare when your COBRA ends, but only if you're still within the eight month special enrollment period that began when your active coverage ended. COBRA does not extend the eight month enrollment period at all.

Kim Humphries · Answer

Yes,  you can sign up for Parts A & B anytime after leaving work.  You have 8 months to start your medicare, but you should do it sooner rather then later.  You should compare the costs between
Medicare and your cobra.  Many times the Medicare A, B, D and a supplement are cheaper then the cobra.  You should at lease compare and contrast those.  It depends on your income a lot of times.  Kim H.

Gary Church · Answer

If you're leaving your employer and considering COBRA, do not choose that option. Instead, make sure to enroll in Medicare and activate your Part A and Part B. After that, you have some alternatives, and I recommend meeting with a licensed Medicare agent who can help you sign up for Medicare and pick the right plan for you.

Alan &quot;AL&quot; Minthorn · Answer

COBRA is NOT viewed as Creditable coverage by Medicare. You should already be enrolled in Part A and adding Part B when your ER plan ends. Most advantage plans are required to cover transition care for treatment in progress for 60-90 days. In many cases, the cost sharing is equal or less than that of ER - COBRA benefits.

Answered by Alan "AL" Minthorn on July 1, 2026

Broker Licensed in ME, FL, NC & NH

Answered by Alan "AL" Minthorn Medicare Insurance Agent

David Moscowitz · Answer

You should go down to the local Social security office to apply for your Medicare card which has the Part A @ part B codes as well as the MBI number.
This will allow you to enroll in a Medicare advantage plan of your choice.

I'm over 65, not enrolled in Part A or B, and leaving active coverage through an employer with 20+ employees for six months of COBRA.

Agents: Share Your Expertise

Seniors: Ask a Question of Your Own

Related Questions

Agent Locator

Medicare Agents Hub
A non-government resource website

I'm over 65, not enrolled in Part A or B, and leaving active coverage through an employer with 20+ employees for six months of COBRA.

Agents: Share Your Expertise

Seniors: Ask a Question of Your Own

Related Questions

Agent Locator

Medicare Agents HubA non-government resource website

Medicare Agents Hub
A non-government resource website