2026 guide. No cost. No pressure.
If you are still working as you approach 65, or your spouse is, Medicare can feel like it showed up uninvited. The decision comes down to a handful of questions. This guide answers them in plain English, in the order you need them.
Pharmacist-led guidance from Dalton Insurance. Licensed in Alabama, Georgia, Florida, Tennessee. Your information is not sold.
The default advice is "sign up at 65." That advice is wrong for some people and expensive for others. These are the three places we see people stumble.
Decision 1
At employers with fewer than 20 employees, Medicare generally pays first once you are eligible, not only after you enroll. Without Medicare in place, the job plan can refuse claims it was never supposed to pay. A multi-employer exception exists. It has to be confirmed in writing, not assumed.
Decision 2
Premium-no-cost Part A still ends your right to contribute to an HSA. When you enroll in Medicare after delaying it, Part A can backdate up to six months. Contributions in that window can become excess contributions. Five minutes of planning, before either clock starts, prevents it.
Decision 3
Your one-time, no-health-questions Medigap open enrollment lasts six months. It starts the first month you have Part B at age 65 or older. After it closes, Alabama does not give you a later birthday rule to switch plans. Nobody sends a reminder when the window ends.
This is the same conversation we have with people who are still on a job plan. It is written so you can use it before you talk to a broker, or bring it with you. No-cost. No upsell inside the guide.
Whether you are still on the job at 70, leaving employer coverage this year, or planning from age 63, the chapters follow the decisions in order. The longer article on the site stays at Working Past 65.
Send me the guideEvery chapter uses a specific situation, with 2026 dollar amounts. Yours will look like one of these.
HSA, large employer
She works at a 250-person company, is 65, and is not taking Social Security. She wants to keep making HSA contributions, including the age-55 catch-up. The guide's path is to delay every part of Medicare on purpose, stop contributions six months before she enrolls, and keep the Medigap window for the month Part B actually starts.
Health changes the math
He is covered on a spouse's 150-employee plan and could have delayed Medicare. A new diagnosis made the deductible and the network the real cost. Moving to Original Medicare with a supplement can raise the monthly premium and still cut the yearly worst case down to the Part B deductible.
The window he kept
She stayed on a large employer plan past 65, never took a Part A card she did not need, and is retiring July 1. Her six-month Medigap window starts when Part B starts, not on her 65th birthday. That is the quiet payoff of delaying the right way.
The guide opens here in plain English, with a printable action plan you can take to HR. Your answers go to the office. Even if you never book a review, it should save you from the penalty and the HSA mistake.
Yes. You give us your name and email, and the guide opens. There is no payment and no required sales call. If you want a person to look at your situation, you say so on the form.
Only if you ask for personal help and choose a phone call. Guide-only requests open the guide and send your answers to the office. You can book a call yourself whenever you want one.
Read chapter 4 of the guide. It includes the exact note to send HR, including the multi-employer exception. Employer size is the question that changes everything else. Guessing is how people pick up a lifetime Part B penalty.
Yes. A lot of people use this at 67, 70, or later, when they are finally leaving a job. Chapter 11 covers CMS-40B, CMS-L564, the 8-month Part B window, and the shorter Part D window.
It can. If you drop the job plan, your spouse and children do not automatically get Medicare. Chapter 9 walks through who needs their own coverage, and how a spouse's active job can be the coverage that lets you delay Part B.
Personal appointments and plan enrollment are available in Alabama, Georgia, Florida, Tennessee. If you live somewhere else, the guide is still yours. The rules in it are federal. Take it to a broker licensed in your state.
Use the guide at your own pace. If you want a person to look at your employer size, your HSA, and your dates, book a no-cost review. No fee to you.