The first Baby Boomers enrolled in Medicare in 2011. They most likely did that through a phone call or in-person appointment with their local Social Security office or a drop-in visit to the office. Back then, there were no horribly long periods spent on-hold or waiting at the office; appointments were available at most offices and easy to make. About that same time, the online system for Medicare enrollment appeared. It was promoted as a more convenient and efficient way to sign up for Medicare. However, most still opted not to enroll online.

But, no matter how they enrolled back then, the process was simpler and Medicare cards usually arrived within a week or two.

Fast forward to 2020. Social Security closed all of its offices in March that year when the COVID pandemic hit. They remained closed for a full two years, even though much of the country had reopened by the summer of 2021. In spite of that, online applications did not skyrocket because many resorted to phone applications. However, add the impact of the largest-ever cut in Social Security staffing in 2024 and the average on-hold time crept up to 2 hours, 32 minutes in January 2025 with about 25 million calls ending without the callers receiving any service. Online enrollment quickly became the most viable option.

Besides the hassles involved with enrolling, there has also been a slowdown in processing applications and sending Medicare cards. The Social Security website, dated November 2022, says, “the beneficiary can expect to receive the Medicare card within two weeks after the SSA processes the initial claim.” My clients report waiting for their cards anywhere from one to three months, with most on the high end of that scale.

There’s one more factor involved in this quagmire. Individuals turning 65 cannot start the enrollment process until the first day of their Initial Enrollment Period, which is three months before their 65^th birthday. Those over 65 can begin three months before they need Medicare to take effect. Because they need their Medicare number to add a Part D drug or Medicare Advantage plan or a Medicare supplement, with only three months to do all this, many are super stressed.

There are a few things that can help relieve this stress and smooth out the enrollment process.

Most Important: A my Social Security Account.

At the top of the list is having a my Social Security account. This account is the primary, secure online portal for managing initial Medicare enrollment.

• If you don’t have an account, create one today. This should be a quick and easy process IF Social Security can verify your identity online. Otherwise, it can take time or maybe even a visit to the local office. (Check out this video and also find information here.)
• If you have an account, try logging in to make sure you have access. If successful, consider doing this regularly so when you need it, you won’t be shut out.

Running into a roadblock when creating an account is an issue and this is probably related to one of three reasons.

1. You did not transition the account to login.gov or ID.me. Since June 2025, Social Security has required an additional layer of security to access your account. You may want to consider login.gov, the official U.S. government’s account. This is run by the GSA, focusing on security with no biometrics for most users.
2. You have a security freeze on your credit reports. You will need to “thaw” your reports temporarily with the three credit bureaus.
3. The information you entered does not match Social Security’s database. This could be related to a different address, name change or some data entry error, such as transposing digits. To resolve this, you may need to take documents to the local office.

Once the account is ready to go, you can enroll in Medicare. After you’ve answered the questions, you have a chance to review and edit your answers. Please double-check that the information is correct, especially any dates. If you make a mistake, you may have to deal with Social Security to correct it.

After receiving a Medicare number, beneficiaries will need to add additional coverage, such as a Part D drug or Medicare Advantage plan or a Medigap policy. Online enrollment can handle this, too.

• For Part D and Medicare Advantage plans, enroll through the Medicare Plan Finder or your medicare.gov account. It is relatively simple and, after answering all the questions, you can print a confirmation of your application.
• Medigap enrollment is handled by each insurance company. The Plan Finder provides phone numbers and website links but online enrollment is done through the plan’s website.

Over-65 Concerns

There are two important prep issues for those over 65 who are still working and have delayed Medicare.

• Watch for and save the notices of creditable prescription drug coverage sent by the plan sponsor every October. If you don’t get one, ask for it. These notices can prevent a Part D late enrollment penalty.
• Get the employer to complete the CMS-L564 form, Request for Employment Information, when retiring. And if changing jobs, get one before walking out the door. This will ward off issues when enrolling in Part B, medical insurance.

Don’t Wait until the Last Minute

At 65 Incorporated, we get calls from those who need Medicare to start in two weeks or at the end of the month. We know they will face turbulence. So, no matter your age, when it’s time for Medicare, start as early as you can.

• Those turning 65 can enroll in the first month of their Initial Enrollment Period. That’s three months before Medicare begins.
• Those over 65 who qualify for a Part B Special Enrollment Period should begin three months before they need Medicare coverage.

Those who need to enroll in Medicare cannot control the time it takes Social Security to do its job, but they can take steps to avoid self-induced delays. Know what needs to be done, then give yourself adequate time to digest and absorb the logic of it all.