The Medigap enrollment period is a six-month window that begins the first month you’re 65 or older, and enrolled in Medicare Part B.
Understanding exactly when this starts could save you from facing medical underwriting that might deny you coverage or charge significantly higher premiums for the rest of your life.
Here’s what the insurance companies don’t advertise: this window isn’t just about getting coverage.
It’s about getting coverage without the medical scrutiny that can leave you paying premium penalties until the day you die.
If you’re in Maryland or Virginia, you have advantages most seniors don’t know exist. But first, let me show you exactly how this system works, and how to navigate it successfully.
The federal government gives you exactly six months to buy any Medigap policy sold in your state without medical underwriting. This window starts the first month you’re 65 or older, and enrolled in Medicare Part B.
During these six months, insurance companies must sell you any policy they offer. They can’t ask about your health. They can’t charge you more for having diabetes, heart disease, or other conditions. They can’t make you wait for coverage to begin.
It’s guaranteed issue protection that exists nowhere else in private insurance.
But here’s the critical timing detail: that window doesn’t start when you turn 65. It starts when you’re 65 and enrolled in Part B. Miss this timing distinction, and you could lose months of protection.
In July 2023, Maryland passed legislation that gives current Medigap policyholders something unprecedented: an annual opportunity to switch plans.
The Maryland birthday rule creates a 30-day window each year, starting on your birthday, where you can switch to any Medigap policy offering equal or lesser benefits, without medical underwriting.
⭐⭐⭐⭐⭐ 5/5 Stars
Turning 65 and finally understanding Medigap thanks to Senior Benefit Services!
I was absolutely overwhelmed when I started looking into Medicare supplement plans. The whole Medigap thing seemed like another language, and I was getting bombarded with confusing mail and sales calls every day. I honestly didn’t know where to turn.
Then I found Senior Benefit Services, and what a difference! My advisor Karen was incredible – she took the time to explain the difference between Plan F, Plan G, and Plan N in terms I could actually understand. She didn’t just push the most expensive option like some other places I called. Instead, she really listened to my health needs and budget concerns.
What impressed me most was how she broke down the costs and showed me exactly what each plan would cover. I ended up saving over $80 a month compared to what I was originally quoted elsewhere, and I actually got better coverage! She explained how my Medigap plan works alongside Original Medicare and even helped me understand when I might need to use it.
Karen was so patient with all my questions (and I had a lot of them!). She never made me feel rushed or like I was bothering her. Even after I enrolled, she checked back with me to make sure everything was working smoothly and reminded me about my annual review.
The whole process was so much easier than I expected. No high-pressure sales tactics, just honest advice from someone who clearly knows the Medicare system inside and out. I’ve already recommended Senior Benefit Services to two of my neighbors who are approaching 65.
If you’re confused about Medigap like I was, don’t waste time with those national call centers. Call these folks – they actually care about finding you the right plan, not just making a sale.
Carol M. Verified Purchase – Plan G Medigap Policy
Your insurance company must notify you 30-60 days before your birthday about this right, but many seniors still don’t know it exists..
Virginia took Maryland’s concept and expanded it. As of July 1, 2025, Virginia residents get a 60-day birthday window, twice as long as Maryland’s protection.
The Virginia rule allows switching to any Medigap policy with identical benefits offered by any insurer in the state. Unlike Maryland, Virginia requires same benefits only, no downgrades allowed.
As someone pointed out in a community thread: “Finally! Been paying high premiums for Plan G because I developed heart issues after my initial enrollment. Now I can shop around every year on my birthday.”
This rule is already influencing the Virginia market. Insurance companies know they’ll face annual competition for every policyholder, which creates competitive pressure on premiums.
If you’re under 65 and on Medicare due to disability, the landscape becomes more complex.
Virginia particularly restricts options for this population. Reddit user shared: “I’m on SSDI and in Northern Virginia. Only Plan A was available until I turn 65. It’s limiting having fewer options when you’re younger and potentially need more coverage.”
The positive development: when you turn 65, you get a new six-month open enrollment period regardless of how long you’ve had Medicare. This is your opportunity to upgrade to comprehensive coverage without medical underwriting.
Outside your initial six-month period, insurance companies can use medical underwriting. This means:
Reddit user shared their reality: “Some have even tried to switch plans after their premiums increased substantially. Only to find out they were denied by multiple companies due to special conditions like, sleep apnea. Then the options are limited, possibly even staying locked into a current plan that is more expensive.”
The financial impact compounds over time. Monthly penalties become annual costs, which become decade-long expenses. For serious conditions, the penalties can be substantial.
Federal law provides some protections called “guaranteed issue rights” that recreate your initial enrollment advantages:
The decision between working with an agent or going solo depends on your comfort with insurance complexity and your specific situation.
Licensed Agents: Can provide deeper carrier knowledge and handle application logistics, but verify their credentials and understand their compensation structure.
When evaluating agencies like Senior Benefit Services, apply the same verification standards you’d use for any major financial decision.
Don’t let Medicare complexity cost you thousands in unnecessary premiums or leave you without switching options when you need them most. The enrollment periods are designed to protect you—but only if you understand how to use them.
Ready to secure your Medicare supplement coverage during your optimal enrollment window? Contact a licensed Medicare specialist who understands both federal rules and your state’s specific protections.
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