In the months before I turned 65 last year, I got a lot of mail from two sources: assisted living centers featuring photos of youthful seniors playing pickleball and Medicare Advantage and medigap providers promoting their plans.
Most of the missives went into the recycling bin. I don’t play pickleball (or plan to sell my house anytime soon), and I was still working. There was no downside to enrolling in Medicare Part A, which covers hospital costs and is free to most beneficiaries. But Part B, which covers doctor’s visits and other outpatient services, comes with a monthly premium — $185 for most retirees in 2025. Since I was already paying for health insurance through my employer, I didn’t want to pay for Part B coverage while I was still working. Earlier this year, however, I decided to retire, and that’s when things got complicated.
Signing up for Medicare Parts B and D
Medicare’s initial enrollment period lasts for seven months, starting three months before the month you turn 65 and ending three months after the month you turn 65. If you fail to enroll during that period, you could be hit with a late-enrollment penalty of 10% of your Part B premium for each 12-month period you weren’t covered, and the penalty will last as long as you have Part B coverage. For example, if you wait two years to enroll, your Part B premium will increase 20%. Medicare Part D, which covers prescription drugs, also has late-enrollment penalties.
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However, if you have health insurance through your job or your spouse’s employer, you can delay enrolling in Part B as long as your coverage is “creditable,” which means that it covers at least as much as Medicare. You must also prove that you had creditable prescription drug coverage when you enroll in Part D. As long as your coverage meets that standard, you have eight months after you leave your job to enroll in Part B and Part D to avoid the draconian late-enrollment penalties. While I had plenty of time to comply, I didn’t want to take any chances — or have any gaps in my coverage after I left my job.
After a few phone calls, I received a document from my employer stating that I had been covered by its insurance. Medicare’s website recommends mailing or faxing the document, but I worried about putting an original document in the mail, and I haven’t used a fax machine since Melrose Place was one of the most popular programs on TV. Instead, I went to a local Social Security branch office, which was very crowded, and left the document in a drop box, hoping that it wouldn’t get lost. It didn’t, but it took a couple of worrisome weeks before I learned I was officially signed up (I’m told this isn’t unusual).
Medigap plans
I opted for original Medicare instead of Medicare Advantage, so I also selected a medigap plan — a supplemental policy that will cover expenses not covered by Medicare — and a Part D prescription drug plan. Medigap plans are provided by private insurers, and each plan has one of 10 letter designations. All plans with the same letter must provide the same coverage, but prices vary, depending on the insurer. I chose Plan G, the most popular option because it provides the broadest amount of coverage.
My choice of Part D plan came down to cost. My medigap provider also offers Part D plans, but its premium for a plan that covers the two prescriptions I take costs about three times as much as the premium for a plan I chose from a different insurer.
My takeaway: When it’s time to enroll in Part B, whether at age 65 or later, start the process early. Getting the correct documents and selecting a supplemental plan that’s right for you takes time. With Medicare coverage in place, I can pursue other goals in retirement — writing, volunteering, reading serious books. Maybe I’ll take up pickleball.
Note: This item first appeared in Kiplinger Personal Finance Magazine, a monthly, trustworthy source of advice and guidance. Subscribe to help you make more money and keep more of the money you make here.
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