Enrollment timing
Identify your Initial Enrollment Period, or confirm whether an employment-based Special Enrollment Period applies.
Free Medicare planning checklist
Turning 65? Learn the Medicare Timeline Before Comparing Coverage.
Organize enrollment dates, current employer coverage, doctors, prescriptions, HSA timing, IRMAA and coverage preferences.
Get the resource
Medicare at 65 Checklist
Coverage structure
Understand Original Medicare, drug coverage, Medicare Advantage and Medigap without assuming one is always better.
Income & HSA
Flag IRMAA and HSA timing questions before enrollment decisions are finalized.
Medicare notice: We do not offer every plan available in your area. Currently we represent 6 organizations which offer 96 products in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options. (Organization and product counts supplied by Advocate Health Advisors for the applicable service area.) Strong Tower Advisors is not connected with or endorsed by the U.S. government or the federal Medicare program.
Who it's for
For anyone within about a year of 65, or leaving a job after 65.
- You will turn 65 in the next 12 months and are not sure when to sign up.
- You are still working past 65 and want to know whether you can delay Part B.
- You or your employer contribute to an HSA.
- You have COBRA, retiree coverage or a Marketplace plan and need to know how it interacts with Medicare.
- Your income is high enough that IRMAA might apply.
What's inside
Dates first, then details, then comparisons.
- Which enrollment path applies to you: automatic enrollment, signing up yourself, delaying Part B with current-employment coverage, or COBRA and retiree situations.
- Enrollment timeline by birth month: a 12-row table showing when your Initial Enrollment Period opens and closes, and when to sign up so Part B starts on the first day of your birthday month.
- Other enrollment windows: General Enrollment, the 8-month employment Special Enrollment Period, fall Open Enrollment, the Medicare Advantage Open Enrollment Period and the one-time Medigap Open Enrollment Period.
- Information to gather at 12 months, 6 months and 3 months before 65: doctors, prescriptions, creditable-coverage notices and your 2024 MAGI.
- HSA timing worksheet: why Medicare.gov advises stopping contributions 6 months before you apply after 65.
- 2026 costs and IRMAA brackets, late-enrollment penalties, questions to ask and common mistakes.
Sample checklist items
- Ask your employer how its plan works with Medicare, and get the answer in writing.
- Ask each current drug plan for its creditable-coverage notice and keep it on file.
- List every doctor, hospital system and prescription, with dosages.
- Set the date to stop HSA contributions.
- Note your 6-month Medigap Open Enrollment window if you choose Original Medicare.
Official 2026 figures included
| Item | 2026 |
|---|---|
| Part B standard monthly premium | $202.90 |
| Part B annual deductible | $283 |
| Part A hospital deductible (per benefit period) | $1,736 |
| Part D annual out-of-pocket threshold | $2,100 |
Source: CMS 2026 Medicare Parts A & B premiums and deductibles; CMS CY 2026 Part D redesign instructions. For free, unbiased one-on-one help, contact your State Health Insurance Assistance Program (SHIP).
Prefer to read first? See Medicare at 65 and Medicare and HSA timing.
Education first
Use the resource to identify the questions that need a deeper answer.
No account transfer or product decision is required to use the guide. Individual recommendations require individual facts and an appropriate advisory process.