Turning 65 with Pennie health insurance is a handoff—not a cancellation project.

Pennie may have done exactly what you needed it to do: provide individual health insurance until you became eligible for Medicare. But when Medicare eligibility arrives, the dates have to be coordinated carefully. Cancel Pennie too soon and you could create a gap in coverage. Leave it running too long and you could lose premium tax credits or potentially have to repay assistance you were no longer eligible to receive.

The objective is simple: your Pennie coverage should end immediately before your Medicare coverage begins.

If you’re turning 65 and currently covered through Pennie, I can help you coordinate your Medicare enrollment, understand when to end your Pennie coverage, and compare Medicare Supplement options. Call or text The DeAngelis Agency at 215-967-8828, or contact us online. There is no charge or obligation.

Excellent
DeAngelis Agency5.0
Based on 161 reviews
Michele Mcquoid
3 days ago
My father needed Medicare supplement part b and Joe was such a big help. He spent alot of time with us to find the correct plan for our needs. If u need help definitely give Joe a call. I will be recommending him to all my friends and family.
Response from the owner:Michele, thank you so much for your wonderful review and recommendation. It was a pleasure helping you and your father find Medicare Supplement coverage that fit his needs. Please don’t hesitate to reach out if either of you has any questions in the future.
Susan Baatz
3 weeks ago
I came across Joe from a postcard that he had mailed out. I am new to Medicare and found him very helpful and knowledgeable. He was able to explain differences in plans and options for my particular needs. I would highly recommend him to anyone that’s transitioning to Medicare.
Response from the owner:Thank you so much for your review Susan. I appreciate your recommendation. If you have any questions or concerns about your Medicare Supplement plan, please reach out.
Andrea Vandeven
3 weeks ago
I used Joe DeAngelis to help me enroll in Medicare, and he made the entire process simple, quick, and stress-free. He provided objective advice and recommended coverage that best fit my healthcare needs while keeping my costs as low as possible. I truly appreciated his knowledge, professionalism, and straightforward guidance. I highly recommend Joe to anyone looking for help navigating Medicare.
Response from the owner:Andrea, thank you so much for your review. It was a pleasure to work with you on your Medicare Supplement Plan selection. Please reach out with any questionsor concerns.
Noreen Gilbert
2 months ago
Joe is so incredibly helpful. His demeanor is plesant. No mattter what questions we have he goes above and beyond to help! Customer Services is impeccable!
Response from the owner:Noreen, thank you so much for your review. It's always a pleasure speaking with you. Please reach out with any questions or concerns about your Medicare Supplement Plan.
Jennifer Leal
2 months ago
Joe was incredibly helpful and helped clarify the Medicare plans/process better than anyone I had spoken to before. He was patient with my questions and helped complete the application easily over a call. I would highly recommend him to anyone looking for help regarding Medicare.
Response from the owner:Jennifer, thank you so much for your review and trusting me with your father's Medicare Supplement coverage. If you have any questions or concerns, please reach out..
Lisa Frushone
2 months ago
Amazing !!I can’t recommend Joe high enough! He handled everything and made this experience stressless and personal which was meaningful to be with an extremely busy schedule!
Response from the owner:Lisa, thank you for your wonderful review and trusting me with your Medicare supplement insurance coverage. I'm glad I was able to make the process simple and easy for you. If you ever have any questions or concerns, please reach out.
Joseph Verhey
3 months ago
Above and beyond service. Don’t go anywhere else. Joe is the guy who makes ā€œI’ve got a guy!ā€ saying come to life. It was like talking to an old friend who cares. Thanks Joe.
Response from the owner:Joe, thank you so much for your review. I really enjoyed our conversation and I'm glad I was able to assist you with your Medicare Supplement Plan selection. If you have any questions or concerns, please reach out!
Nancy Poinsett
3 months ago
Joe made the medicare process easy and understandable. I highly recommend using him for your medicare insurance needs.
Response from the owner:Thank you, Nancy, for your kind review and for trusting me with your Medicare coverage. It was a pleasure helping you, and I truly appreciate the opportunity to work with both you and Keith. Thank you for your recommendation.
Richard Jaynes
3 months ago
I contacted Joe DeAngelis for Medicare assistance, and he answered all my questions and guided me with some steps I was not aware. Joe was super friendly and easy to talk to. I was totally satisfied with Joe and appreciative how he wanted all my questions answered and he made himself available for any future questions. Call Joe if you want a pleasant experience!! He is the best! Rich J.
Response from the owner:Rich, thank you so much for your review. I was happy to help you with your Medicare Supplement Plan selection. If you should have any questions or concerns, please reach out.
ivan doner
3 months ago
Response from the owner:Thank you for your review, Ivan. It was a pleasure to meet with you and Chris. Please reach out with any questions.
Christine Doner
3 months ago
Excellent presentation! Great customer service!
Response from the owner:Thank you for your review, Chris. It was a pleasure to meet with you and Ivan. Please reach out with any questions.
Colette Spera
3 months ago
Joe is 5 stars * * * * * hands down. He is polite, knowledgeable and extremely efficient in explaining the entire Medicare experience for me. It's was a bonus that we went to high school together and lived down the street from one another. I highly recommend him to anyone navigating a new "turning of 65" and applying for Medicare coverage. A+++++++++++++++++++++++++++++
Response from the owner:Thank you so much for you most excellent review, Colette. It was a pleasure catching up with a High School mate after all these years. Please reach out with any questions or concerns.
Rick Bott
4 months ago
Ver easy to work with; the easiest part of the process was talking to Joe. He got me all set in 30 minutes. Highly recommend.
Response from the owner:Rick, thank you so much for your review! It was great to work on your Medicare Supplement Plan selection. If you have any questions about your Plan N Medicare Supplement Plan, please reach out.
Lisa Hartman
5 months ago
Joe was great! Happy to have him as my insurance broker
Response from the owner:Thank you so much for your review, Lisa! It was a pleasure to work with you on your Medicare Supplement Plan enrollment. Please reach out with any questions or concerns.
john schmidtberger
5 months ago
Friendly, helpful, knowledgeable. Easy to reach. Helped me out when I hit a tech problem with a third-party application!
Response from the owner:John, it was a pleasure helping you with your Medicare Supplement coverage and I'm glad to hear it was easy for you. If you have any questions or concerns, please reach out.
Passing Through
5 months ago
Good morning everyone. want to give special thanks to Joe he is a godsend, for those who have reached golden age helping people navigate their way through signing up for Medicare and making the right choices that fit your need for supplements for part B . so I hope that anyone needs a Medicare advisor Definitely consider Joe for his kind patience and knowledge Sincerely Robert & Brenda
Response from the owner:Thank you so much for your review Brenda. It was a pleasure working on your Medicare Supplement plan with you. Please reach out if you have any questions or concerns.
Floss Hauschild
6 months ago
Can't believe how shell-shocked and overwhelmed I felt when trying to navigate my way through the Medicare sign-up process. Thank goodness for people like Joe, who are infomative and intellegent enough to lend a hand and help people like myself figure all this out! I was evaluated and directed to plans that meet my personal needs Thanks Joe for all you do. You saved me major agita!
Response from the owner:Thank you so much for your excellent review, Floss. I'm glad I was able to save you from "major agita"! šŸ™‚ It was a pleasure working with you on your Medicare Supplement Plan. If you should have any questions moving forward, please reach out.
Robert DiMatteo
6 months ago
Easy going and very helpful. Joe made the whole process less nerve wracking overall. I would highly recommend him to anyone turning 65 and wondering what to do about all of this.
Response from the owner:Thank you for your review, Robert. Please reach out if you have any questions or concerns about your Medicare Supplement Plan.
Fred Kaissi
7 months ago
Joe DeAngelis is friendly, attentive, and very knowledgeable. He takes the time to explain Medicare in a clear, easy-to-understand way. I really appreciate his guidance and would recommend him to anyone.
Response from the owner:Thank you for your review, Fred. Please reach out if you have any questions or concerns about your Medicare Supplement Plan
dave hampton
7 months ago
Fantastic service, made changing plans effortless and understandable. Joe was extremely helpful. Highly recommended!
Response from the owner:Thanks for your review, Dave. It was a pleasure to work with you and I'm always glad to meet one of my neighbors! Please reach out if you have any questions or concerns.
Kathy Sincavage
10 months ago
Joe made the process of enrolling in a supplement plan so easy and advised on a part D plan. We really appreciated his expertise and guidance. Highly recommend him.
Response from the owner:Kathy, thank you so much for your review, please reach out with any questions or concerns.
Daryl Farrell
10 months ago
We wanted to switch plans and Joe made the process so easy!
Response from the owner:Daryl, it was a pleasure helping you with your Medicare Supplement coverage and I'm glad to hear it was easy for you. If you have any questions or concerns, please reach out.
Shirley Calvert
10 months ago
Joe is kind and extremely knowledgeable. The right person to help navigate the challenges of Medicare. I will recommend him to all my friends and family as the go to person for all their Medicare needs.
Response from the owner:Shirley, it was a pleasure helping you with your Medicare Supplement coverage and I'm glad to hear it was easy for you. If you have any questions or concerns, please reach out.
Jean Seward
11 months ago
Joe is very knowledgeable and is easy to communicate with. Very personable. This is t 2nd time he has helped with Medicare benefits with ease. Thanks Joe
Response from the owner:Jean, I'm glad I was able to help you again with your Medicare Supplement Plan. Please reach out with any questions.
Dale Beirn
11 months ago
Joe explained the different plans which made everything clearer to choose a plan Medicare that would fit my needs. I would definitely recommend his company to others that are struggling to figure out Medicare.
Response from the owner:Dale, it was my pleasure helping you with your Medicare Supplement coverage and I'm glad to hear it was easy and made clear for you. If you have any questions or concerns, please reach out.

Pennie Did Its Job—Now Medicare Needs a Clean Handoff

People sometimes hesitate to leave Pennie because the coverage is working, the premium is affordable, or they finally understand how their plan operates.

That is completely understandable. But Pennie coverage is generally a bridge to Medicare—not a reason to postpone Medicare enrollment.

The important question is not, ā€œCan I keep my Pennie plan?ā€

The better question is, ā€œWhat should replace it, and on what exact date?ā€

For most people becoming eligible for premium-free Medicare Part A, continuing to receive Pennie premium tax credits is not an option. Pennie coverage also does not become a Medicare Supplement simply because you turn 65. It does not fill the deductibles and coinsurance left by Original Medicare, and it does not replace the need to make a timely Medicare Part B decision.

This is why I treat the transition as a date-coordination problem first and an insurance-shopping problem second.

First, make the dates line up. Then decide which Medicare coverage fits you.

The Three Clocks You Need to Coordinate

Most Pennie-to-Medicare mistakes happen because people think there is one enrollment deadline. In reality, three separate clocks may be running.

1. Your Medicare Initial Enrollment Period

Your Medicare Initial Enrollment Period normally lasts seven months:

  • The three months before the month you turn 65
  • The month you turn 65
  • The three months after your birthday month

When you enroll can affect when Medicare begins. People already receiving Social Security benefits may be enrolled automatically, while others must actively apply through Social Security.

Do not assume that having Pennie coverage gives you the same right to delay Medicare Part B as active employer group coverage.

2. Your Pennie Termination Date

Pennie coverage does not automatically terminate when Medicare begins.

You should generally arrange for Pennie coverage to end the day before Medicare starts. For example, if Medicare begins September 1, the usual goal is to have Pennie coverage end August 31.

Do not cancel Pennie before confirming your Medicare effective date.

3. Your Medicare Supplement Open Enrollment Period

Your one-time federal Medicare Supplement Open Enrollment Period lasts six months. It begins on the first day of the month in which you are both:

  • At least 65 years old
  • Enrolled in Medicare Part B

During this period, an insurance company generally cannot decline your Medicare Supplement application or increase your premium because of your health.

After this period ends, changing or purchasing Medicare Supplement coverage may require medical underwriting unless you qualify for a specific guaranteed-issue right.

Your Medicare enrollment deadline and your Medicare Supplement opportunity are related—but they are not the same thing.

Pennie Coverage Does Not Automatically End When Medicare Starts

This is one of the most consequential details in the entire transition.

Medicare does not call Pennie and cancel your Marketplace plan for you. Pennie does not necessarily know that it should terminate your coverage simply because you received a Medicare card.

You or someone authorized to assist with your Pennie account must update the application and request the appropriate termination date.

A clean transition normally looks like this:

  • Confirm the effective dates for Medicare Part A and Part B.
  • Select the Medicare coverage that will begin with Medicare.
  • Schedule Pennie to end on the final day before Medicare starts.
  • Verify that the termination affects the correct person—not necessarily everyone in the household.
  • Save the termination confirmation.

Pennie allows consumers to manage enrollment through their online accounts. Assistance is also available from Pennie at 1-844-844-8040.

The order matters. Confirm Medicare first. Then terminate Pennie.

Pennie Is Not Active Employer Coverage

This distinction is easy to miss and expensive to get wrong.

Someone covered by an active employer group health plan may be able to delay Medicare Part B without a late-enrollment penalty, depending on the employment and plan circumstances.

Pennie is individual Marketplace coverage. It is not coverage based on your or your spouse’s current employment.

Remaining on Pennie after 65 generally does not protect you from the potential consequences of delaying Medicare Part B. Those consequences may include:

  • A gap before Medicare coverage can begin
  • A permanent Medicare Part B late-enrollment penalty
  • Delayed access to a Medicare Supplement
  • Loss of Pennie premium assistance
  • Responsibility for medical expenses the Pennie plan may not cover as expected after Medicare eligibility

COBRA, retiree coverage, Pennie coverage, and active employer coverage are not interchangeable. Each must be evaluated under its own Medicare rules.

What Happens to Your Pennie Premium Tax Credits?

Many Pennie members receive advance premium tax credits that reduce their monthly insurance premium.

Once you become eligible for premium-free Medicare Part A, you are generally no longer eligible for Marketplace premium tax credits. That can be true even if you fail to enroll in Medicare when you first become eligible.

Continuing to collect premium assistance after losing eligibility could result in some or all of that assistance being reconciled when you file your federal tax return.

That is why ā€œI’ll just keep Pennie for another few monthsā€ can be more complicated than it sounds.

There are less-common situations in which someone does not qualify for premium-free Part A. Those cases need individualized review because the Marketplace and Medicare rules can operate differently.

What If Your Spouse Is Younger Than 65?

This is where a careful handoff becomes especially important.

Suppose you and your 62-year-old spouse are covered under the same Pennie plan. You are turning 65, but your spouse is not eligible for Medicare.

You normally do not want to cancel the entire household’s Pennie coverage.

Instead, the Pennie application should be updated so that:

  • Your Pennie coverage ends when your Medicare coverage begins.
  • Your younger spouse remains enrolled through Pennie.
  • Household and tax information remains accurate.
  • Pennie recalculates any financial assistance available to the remaining enrollee.
  • The replacement plan and premium are confirmed before the change is finalized.

Family members generally still need to be included correctly on the Marketplace application even when only certain people need Pennie coverage.

Do not assume that removing one person will leave the remaining premium and subsidy unchanged. Pennie should recalculate the household’s eligibility.

A Practical Pennie-to-Medicare Example

Suppose Linda turns 65 in November. Her husband, Mark, is 62. They are both insured through Pennie.

Linda confirms that Medicare Parts A and B will begin November 1.

Her transition could look like this:

During August

Linda begins her Medicare enrollment and coverage review. She compares Original Medicare with Medicare Advantage and considers whether a Medicare Supplement and Part D prescription drug plan fit her needs.

During September and October

Linda selects her Medicare coverage with a November 1 effective date. She verifies the effective dates in writing rather than relying solely on an application submission date.

Linda and Mark then update their Pennie application. Linda requests an October 31 termination date for her coverage. Mark remains on Pennie, and the household confirms his new premium and financial assistance.

On November 1

Linda’s Medicare Parts A and B begin. If selected, her Medicare Supplement and Part D coverage also begin.

Mark continues with Pennie.

There is no intentional gap, no unnecessary overlap, and no accidental cancellation of Mark’s insurance.

This example is simplified, but the principle is the same: one household may need two different insurance systems working at the same time.

Choosing Medicare Coverage After Pennie

Leaving Pennie does not automatically determine which type of Medicare coverage you should choose.

Your principal choices will generally include:

  • Original Medicare with a Medicare Supplement and a separate Part D plan
  • A Medicare Advantage plan that provides Medicare benefits through a private insurer

For people interested in predictable medical expenses and broad provider access, Medicare Supplement Plan G and Plan N are often worth comparing.

Plan G provides more complete coverage of the gaps left by Original Medicare. Plan N can offer a lower premium in exchange for certain office and emergency room copayments and no coverage for Medicare Part B excess charges.

Pennsylvania prohibits providers from billing Medicare Part B excess charges for services performed in Pennsylvania. That can make the excess-charge difference less significant for Pennsylvania residents receiving their care in the state. Travelers should still understand that another state’s rules may be different.

Plan N is not automatically the better deal simply because its monthly premium is lower. The decision should account for:

  • The actual premium difference between Plan G and Plan N
  • Expected office and emergency room visits
  • Household discounts
  • Historical and requested carrier rate increases
  • Pricing method
  • Carrier stability
  • Underwriting rules that could affect a future change

The lowest first-year premium is not necessarily the lowest long-term cost.

Common Pennie-to-Medicare Mistakes

 

Canceling Pennie Before Medicare Is Confirmed

An application receipt is not the same thing as a confirmed Medicare effective date. Do not create an avoidable coverage gap.

Assuming Medicare Will Cancel Pennie

It generally will not. Pennie must be updated separately.

Treating Pennie Like Active Employer Coverage

Pennie is individual Marketplace insurance. It generally does not create the same Medicare Part B Special Enrollment Period protections as coverage from current employment.

Keeping Premium Tax Credits After Medicare Eligibility

Eligibility for premium-free Part A generally ends eligibility for Marketplace premium tax credits. Waiting to update Pennie can create an unpleasant tax problem.

Canceling Coverage for the Whole Family

If a spouse or dependent still needs Pennie, the application must be changed carefully. The Medicare-eligible person may be leaving Pennie while everyone else remains.

Waiting Too Long to Consider a Medicare Supplement

Your Medigap Open Enrollment Period is valuable. Do not wait until it is nearly over to discover that your preferred coverage, carrier, or rate requires more planning.

What I Recommend

Start the process approximately three months before the month you turn 65.

At that point, establish a simple transition calendar containing:

  • Your 65th birthday
  • Your Medicare enrollment window
  • Your confirmed Medicare Part A and Part B effective dates
  • Your final day of Pennie coverage
  • Your Medicare Supplement or Medicare Advantage effective date
  • Your Part D effective date, if applicable
  • The coverage arrangements for a younger spouse or dependents

You do not need to become a Medicare expert. You do need to make the right decisions in the right order.

Frequently Asked Questions

Can I keep Pennie after I turn 65?

You may be able to keep an unsubsidized Marketplace policy, but it does not replace Medicare, coordinate with Medicare like a Supplement, or protect you from Medicare late-enrollment penalties. Most people eligible for premium-free Part A should transition to Medicare when first eligible.

Will Pennie automatically cancel when Medicare starts?

No. Pennie coverage generally must be terminated separately. Confirm Medicare first, and then schedule Pennie to end immediately before Medicare begins.

When should I cancel my Pennie plan?

The usual objective is for Pennie to end on the final day before Medicare starts. If Medicare begins September 1, Pennie would generally end August 31.

Can my younger spouse remain on Pennie?

Yes. A younger spouse may continue Pennie coverage after you move to Medicare. The application must be updated carefully so that only the appropriate person’s coverage ends and Pennie can recalculate the remaining household’s premium assistance.

Does Pennie let me delay Medicare Part B?

Pennie is not active employer group coverage. It generally does not give you the same protection against Part B late-enrollment penalties and delays.

Can Pennie coverage work as a Medicare Supplement?

No. A Medicare Supplement works with Original Medicare. Pennie Marketplace insurance is not Medigap coverage.

Will I need medical underwriting for a Medicare Supplement?

Not during your six-month Medigap Open Enrollment Period. After that period, medical underwriting may apply unless you qualify for a guaranteed-issue right.

Can a Medicare broker help coordinate the transition?

A Medicare broker can help confirm the Medicare timeline, explain Original Medicare, Medicare Supplement, Medicare Advantage, and Part D options, and arrange Medicare coverage to begin on the correct date. Pennie account changes should be completed through Pennie or with authorized Pennie assistance.

Related Medicare Topics

Turning 65 Medicare Checklist
Should I Take Medicare at 65 If I’m Still Working?
Leaving Employer Coverage for Medicare: A Step-by-Step Guide
Plan G vs. Plan N in Pennsylvania
What Is a Medicare Supplement?

Related Local Pages

Medicare Supplement Broker in Doylestown, Pennsylvania
Independent Medicare Broker in Bucks County
Medicare Broker in Montgomery County
Glenside Medicare Broker
Abington Medicare Broker
Southampton Medicare Broker
Newtown, Pennsylvania Medicare Broker

Schedule Your Medicare Consultation Today

Medicare can be confusing, but getting answers shouldn’t be.

Whether you’re enrolling for the first time, reviewing your current coverage, considering a plan change, or simply looking for a second opinion, I’m happy to help you understand your options and answer your questions.

I’ve been helping Medicare beneficiaries since 1985, and I’ve built my practice on straightforward advice, long-term relationships, and treating people the way I’d want my own family treated.

If you’d like to discuss your Medicare options, call or text The DeAngelis Agency at 215-967-8828.

Click here to ask a question.

There’s no pressure and no obligation—just honest guidance to help you make a confident decision.

turning 65 with Pennie health insurance in Pennsylvania