D Is for Delay

Richard Connor

REMEMBER THE OLD sayings that “the cobbler’s children have no shoes” and “the carpenter’s house is falling down”? That’s how I felt last month as I frantically tried to enroll in Medicare.

My 65th birthday was in early September. Medicare has an initial enrollment period that lasts seven months. It starts three months before you turn age 65, includes your birth month, and ends three months after the month you turn 65. Suppose you were born on Sept. 15. Your open enrollment period would begin June 1 and last until Dec. 31.

If, say, you’re still working at age 65 and have health care coverage through your employer, special rules apply to Medicare enrollment and to when benefits begin. What if you aren’t covered by one of the exceptions? If you’re currently receiving Social Security benefits, you should be automatically enrolled and you’ll receive your Medicare card before your 65th birthday. This happened to a friend of ours—a widow—who was receiving Social Security survivor benefits.

What if you aren’t yet receiving Social Security? You’ll need to apply for Medicare and, if you want coverage to start in the month you turn age 65, you should submit your application no later than the month before. I understood that timeline. Problem is, I got hung up researching and choosing among Medigap plans, those add-on insurance policies that help cover what Medicare doesn’t.

My previous employer’s pension plan offers a Part B supplement plan and a Part D drug coverage plan. About three months prior to my 65th birthday, the company sent me a detailed package and enrollment forms. Unfortunately, I misplaced the package. I requested another one, but it took time to arrive.

My mistake: I should have applied for Medicare while I waited for the information and before I settled on a Medigap and Part D drug policy. The fact is, you need to enroll in Medicare before you can apply for these supplement policies. I wised up and, on Aug. 25, applied for Medicare Parts A and B through my online Social Security account. This should have ensured my coverage would start Sept. 1.

But things didn’t go smoothly. A few days later, I received a letter requesting an original birth certificate to verify my date of birth. I could mail it or drop it off at a local office. The Social Security Administration (SSA) would then return the birth certificate once it had verified my date of birth.

Recent articles talked of long lines and extensive waits as the SSA reopened offices this past April. I learned that offices were still observing COVID-19 protocols. Despite this, I drove to a local office to drop off my birth certificate in person. I reasoned I could speak to an agent to make sure there was nothing else required.

The line outside the local SSA office was a dozen deep. The office allowed just six people in at a time. When one person left, the friendly security guard let another person in. After about 30 minutes, the security guard came out and asked if anyone was only dropping off documents. He explained that I could enter the office, place my document in a special envelope and drop it in a secure box.

Three days later, I received another letter from the SSA, returning my birth certificate, and requesting that I mail in or bring to an office my birth certificate and ID. Yes, the SSA was asking for the same document it had just returned.

This confused me. The letter supplied a phone number for the local office, so I called to get clarification. Amazingly, an agent answered on the third ring. I explained my confusion and she looked up my file. I was concerned when she let out a perplexed “huh.” She told me that my first name was misspelled on my online Social Security account. I’ve had that account for at least a decade. Somehow, my first name was spelled with an extra “D” at the end.

She apologized and said this should have been communicated to me. She told me I needed to come to the office with two forms of identification, plus an original birth certificate, and apply for a replacement Social Security card. This was on a Friday afternoon. The office was open for a few more hours. I thought that maybe it wouldn’t be too crowded.

I rushed over and joined a substantial queue. An hour later, the line hadn’t moved. It was obvious I wasn’t getting in that day. I returned Monday morning 30 minutes before the office opened. I was fourth in line. Twenty minutes later, they let six of us in. About 15 minutes after that, I was at a window talking with a live agent.

She was polite and helpful. She took my documents and created the application for my replacement Social Security card. She then reviewed my Medicare application and said it had been approved. I should receive a new card, as well as my Medicare ID card, within a few weeks, the agent said.

When I got home, I checked my online Social Security account. Sure enough, the Medicare application section of my account had been updated to say my application had been approved. I was able to create an account on and print an ID card.

Waiting in line at the office, I heard horror stories from my queue-mates. One woman had received benefits as a child when her father died prematurely. She had recently received a letter from the SSA saying she had to repay some of those benefits—benefits she’d received in the 1970s.

Still, I have to say that the SSA employees I dealt with at the office were very professional. They’re on the frontline of an enormous bureaucracy and deal with people who are frustrated, confused and scared. I don’t envy them.

Over the next few weeks, it all came together. I enrolled in Medigap and Part D supplement plans. I received my official Medicare ID card, a new Social Security card and the supplement plan ID cards. I’ve been able to register my new insurance information with all of my doctors.

The lesson of my saga is clear: Don’t wait. If you don’t yet have an account on Social Security’s website, create it now. It’s easy to apply for benefits online and monitor the progress of your applications. Do your research before your enrollment period begins. After all, you never know what gremlin is lurking in the system that’ll hold things up. Take it from me—your friend Richardd.

Richard Connor is a semi-retired aerospace engineer with a keen interest in finance. He enjoys a wide variety of other interests, including chasing grandkids, space, sports, travel, winemaking and reading. Follow Rick on Twitter @RConnor609 and check out his earlier articles.

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