The Medicare Playbook
The Medicare Playbook: know the court before you play.
Medicare is a set of connected choices, not one decision — and missing a window can mean a penalty that follows your premium for good. This playbook walks the whole match: the parts, the deadlines, and the faults that catch people off guard.
Watch
See the Playbook in action.
The playbook
Five pages. The whole court.
Know the Court (what each part does), Court Management (five moves to get more from your coverage), Stay Out of the Kitchen (the clocks that carry penalties), and Avoid Faults (the six mistakes we see most) — with 2026 costs and a checklist for your next conversation.
Written for people turning 65, people already on Medicare who haven’t looked at their coverage in a while, and the families helping them.
What’s inside
Know the court
What Parts A, B, C, D, and Medigap each actually do, and which ones can’t be paired.
Set your formation
Five moves for getting more from your coverage — run your drug list, verify a plan takes it, document proof you can delay, price the bad-case year, review every fall.
Stay out of the kitchen
The two different penalty clocks — Part B runs for as long as you have it, Part D has its own 63-day-gap trigger — so you know which one applies before you let coverage go.
Avoid the faults
Five specific mistakes: treating every deadline the same, trusting COBRA/retiree coverage as current-employment coverage, HSA contributions that must stop, choosing by premium alone, set-and-forget renewal.
The windows that matter
Medicare runs on more than one clock. Here is each window, what it’s for, and what happens if you miss it.
| Window | What it’s for | If you miss it |
|---|---|---|
| Initial enrollment — 7 months around 65 | Enroll in Parts A and B; choose drug coverage | Coverage delays or penalties may apply |
| Part B special period — 8 months | After current job-based coverage ends | General Enrollment may be your next chance |
| Part D — 2 full months | After creditable drug coverage ends | A 63-day gap may trigger a penalty |
| General Enrollment — Jan 1 to Mar 31 | Catching up on Part B | Coverage starts the next month |
| Medigap — 6 months | Starting from Part B at 65 or older | Medical underwriting may apply later |
| Open Enrollment — Oct 15 to Dec 7 | Changing Medicare Advantage or Part D | Wait for another window |
First-of-the-month birthdays follow a shifted timeline. Confirm exact dates at Medicare.gov.
Three ways to set up your side of the court
There’s no single right answer. There’s the setup that fits your doctors, your drugs, your travel, and your budget.
Play singles
Original Medicare + Part D. Separate A, B, and drug coverage, with provider flexibility. Trade-off: you manage the pieces, and Original Medicare alone has no annual out-of-pocket limit.
Bring a partner
Original Medicare + Medigap + Part D. Broader access and steadier costs, since Medigap helps cover some Original Medicare gaps. Trade-off: separate premiums can make monthly costs higher.
The all-in-one play
Medicare Advantage. One coordinated plan that usually includes drugs and an annual out-of-pocket limit. Trade-off: networks, prior authorization, referrals, and yearly changes may apply.
The scoreboard: 2026 costs
Published Medicare figures for 2026. They change every year, and help is available for people who qualify.
A late Part B enrollment costs real money: generally about 10% more for each full year you went without it. Three years late is roughly +30%, about $61 a month on the 2026 standard premium, and it generally lasts as long as you have Part B. Medicare Savings Programs and Extra Help may reduce what you pay.
Medicare isn’t one decision — it’s a set of connected choices
Most guides treat Medicare like a single form to fill out. It isn’t. Part A, Part B, Part C, Part D, and Medigap are five different pieces that interact — and a choice about one changes what’s available or advisable for the others. The myth is that Medicare is free and covers everything. The reality: most people have costs, and Original Medicare generally excludes routine dental, vision, and hearing care. The right coverage isn’t a rule of thumb, and it isn’t automatically what your neighbor picked. It’s whatever fits your side of the court.
The parts, in plain terms
Part A (Hospital) covers inpatient care, qualifying skilled nursing, hospice, and some home health care — premium-free for most, but not cost-free. Part B (Medical) covers doctors, outpatient care, preventive services, and equipment, and carries a monthly premium. Part C (Medicare Advantage) is a private-plan alternative that bundles A and B, usually with drug coverage — networks and rules vary by plan. Part D (Prescriptions) is drug coverage, either stand-alone or built into most Advantage plans; a 63-day gap without creditable drug coverage can trigger a penalty. Medigap (Medicare Supplement) helps cover some Original Medicare gaps, but it cannot be paired with Medicare Advantage.
The windows that actually matter
Missing a window doesn’t just mean waiting — for Part B and Part D, it can mean a penalty that follows your premium indefinitely. The two parts don’t share a clock: Part B’s penalty runs about +10% for every 12-month period you went without coverage you should’ve had. Part D’s penalty is a different formula, and can be triggered by a 63-day gap in creditable drug coverage. The smart move is knowing which clock is running before you let any coverage lapse — particularly if you’re still working past 65, where the rules depend on employer size, HSA contributions, spousal coverage, and COBRA or retiree-plan status. COBRA and retiree coverage are not current-employment coverage for Part B purposes.
Who this is for
Anyone approaching 65, anyone already on Medicare who hasn’t reviewed their coverage since they enrolled, and anyone with a spouse in either position. Working families, farmers, and small business owners across Kentucky and Tennessee have been bringing exactly these questions to Studle since 1985 — this playbook, built with Medicare partner John Phelps, is the same conversation in writing.
Get your free copy
Tell us your name and email and the playbook opens right away. We’ll also email you the link. No cost, no strings — just the game plan.
Bring to the conversation
- Your exact enrollment dates
- Doctors and hospitals you want to keep
- Medications, doses, and pharmacy
- Your travel pattern and any second address
- Medical and drug coverage notices
Related
Medicare Education
Reserve a seat at a session or ask a question.
Retirement Planning
How Medicare fits the rest of your plan.
Studle Financial Services provides Medicare education. Plan enrollment is handled with a licensed, independent Medicare partner, and Studle may be compensated when a plan is enrolled. We do not collect health information on this website. Medicare has neither reviewed nor endorsed this information.
Educational use only. Not connected with or endorsed by the U.S. government or the federal Medicare program. Verify current figures at Medicare.gov.
Lighting the way to a brighter financial future.
Family-owned since 1985. Real people helping real people across Kentucky and Tennessee.
Services
Studle
Visit or call
164 Old Porter Pike
Bowling Green, KY 42103
270.438.2611
Fax 270.495.3888
Monday–Friday, 8:30–5:00
Studle Financial Services provides financial guidance and insurance products to families and businesses in Kentucky and Tennessee. Information on this website is for educational purposes and is not individualized advice. Your situation is unique — please talk with a licensed professional before making financial decisions.
Tax preparation and filing services are provided by Studle & Associates. Studle Foundation is the charitable arm of the Studle family of companies.
© 2026 Studle Financial Services · 164 Old Porter Pike, Bowling Green, KY 42103 · Privacy Policy · Disclosures · Accessibility