Turning 65. Here is the order to do things in.
Eight things, in the order they need to happen. If you are already past one of them, that is usually fine, and the page says so.
-
4 to 6 months before
Answer one question: will you still have coverage from a job?
Yours or a spouse’s, and does that employer have 20 or more employees? Get the answer from the benefits office in writing if you can. Everything after this depends on it.
-
3 months before
Apply for Part A and Part B through Social Security
Online at ssa.gov, or by phone. Doing it now means your coverage starts on the first day of your birthday month. If you are already drawing Social Security, this happens automatically and your card arrives in the mail.
-
3 months before
Write down your prescriptions and your doctors
Exact drug names, doses and how often. Every doctor you want to keep, including the ones you see once a year. This one list is what an honest comparison is built from, and it takes ten minutes.
-
2 months before
Decide the shape: supplement or Advantage
Original Medicare plus a Medigap policy, or a Medicare Advantage plan. This is the fork in the road. It is about your doctors, your travel and your appetite for surprises, not about which is cheaper this year.
-
1 to 2 months before
If you chose a supplement, apply inside your six-month window
The six months that begin when you are both 65 and enrolled in Part B are the only time a company must accept you regardless of your health. Applying inside it is the difference between a guaranteed yes and a maybe.
-
1 month before
Choose the drug plan by total yearly cost
Not by monthly premium. Run your real prescription list against the plans sold in your county and compare what you would actually spend across the year, pharmacy by pharmacy.
-
The month it starts
Check the card, then book the free welcome visit
Make sure the effective dates on your card are what you expected. Then book your Welcome to Medicare visit, which is free in your first twelve months on Part B and sets a baseline.
-
Every fall after
Re-check between October 15 and December 7
Formularies and networks change every January. The plan that was right this year is not automatically right next year, and the letter telling you what changed will not lead with the part that matters.
Three ways people get this wrong
Assuming COBRA counts as employer coverage
It does not, for Medicare purposes. COBRA is not coverage from active employment, so it does not give you a Special Enrollment Period for Part B. People stay on COBRA past 65, then discover a lifelong penalty and a wait until the next January.
Contributing to an HSA after Medicare starts
Once any part of Medicare begins, you can no longer put money into a health savings account. Worse, Part A can be backdated up to six months when you apply late, which can make contributions you already made ineligible. Stop contributing six months before you plan to enroll.
Choosing a drug plan on its monthly premium
A $0 drug plan that puts one of your medications in a high tier can cost you more across a year than a $40 plan that covers it well. Compare the yearly total for your actual prescriptions, at your actual pharmacy.
What if you are already past 65?
Then the question is which window you are in now. If you are still working with employer coverage, you likely have a Special Enrollment Period waiting for you when that job ends. If you are not, and you never enrolled, the General Enrollment Period runs January 1 to March 31, and there may be a penalty we should work out before you do anything.
Either way, one phone call establishes which of these you are in. See every enrollment window, or just call.
Tell us your birthday. We will tell you your dates.
That is the whole call. If you are early, we will say so and tell you when to call back. We do not keep lists and we do not sell anyone’s details.