Medicare Enrollment Explained 2026: Working Past 65, COBRA and the Late-Enrollment Penalty

Most people assume Medicare enrollment is simple: you turn 65, you sign up. For a lot of people that is exactly right. But if you are still working at 65, covered under a spouse's employer plan, holding COBRA, carrying retiree insurance, or contributing to an HSA, the answer changes — and getting it wrong can mean a gap in coverage or a penalty you pay for the rest of your life. David Heitner walks through the Medicare enrollment rules that actually decide your timing. In this video: 0:00 - Why timing matters as much as coverage 1:07 - Your Initial Enrollment Period 1:55 - Do you have to enroll at 65? 2:29 - Why employer size changes the answer 3:27 - Part A, and why your HSA matters 4:31 - Retiring after 65: the eight-month window 5:13 - COBRA is not active employer coverage 6:05 - What about retiree coverage? 6:47 - The Part B late-enrollment penalty 7:30 - Part D has a late-enrollment penalty too 8:29 - If you miss your enrollment window 9:04 - Automatic enrollment, and when it isn't 9:46 - A simple timeline 10:41 - Why one general rule doesn't fit 11:32 - What's next: IRMAA This is Episode 8 of an ongoing series covering the foundation, Part A, Part B, Medicare Supplement insurance, Medicare Advantage, choosing between the two paths, and Part D. Episode 9 covers IRMAA — the income-related surcharge on Medicare premiums. The enrollment rules used in this video: Initial Enrollment Period: seven months, beginning three months before the month you turn 65 and continuing three months after Employer size: for many people 65 or older, a group health plan at an employer with 20 or more employees generally pays first; with fewer than 20 employees Medicare generally pays first Special Enrollment Period for Part B: generally eight months, beginning when employment ends or when coverage based on current employment ends, whichever happens first General Enrollment Period: January 1 through March 31, with coverage generally beginning the month after you sign up Part B late-enrollment penalty: generally 10% for each full 12-month period you could have had Part B but did not enroll, and in most cases paid for as long as you have Part B Part D late-enrollment penalty: generally triggered by 63 days or more without Medicare drug coverage or other creditable prescription drug coverage Worth knowing: COBRA and retiree insurance are generally not treated the same way as coverage based on current employment when it comes to delaying Part B. If you are Medicare-eligible when you leave your job, staying on COBRA does not reliably postpone your Medicare enrollment deadline. That single assumption is one of the most expensive mistakes in this episode. Also worth knowing: once you are enrolled in Medicare you are no longer eligible to contribute to a Health Savings Account, and Part A coverage can begin retroactively for up to six months when someone enrolls after 65 — though not earlier than the month you turned 65. If you are working past 65 and still funding an HSA, settle the timing before you retire. FREE GUIDE - Medicare Insurance Basics (PDF): https://drive.google.com/file/d/1GHbM... More Medicare resources: https://heitsbenefits.com/medicare/?u... Questions about your own situation: Call or text (201) 647-2095. Heits Benefits Group does not offer every plan available in your area. Any information provided is limited to the plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options. Not connected with or endorsed by the U.S. Government or the federal Medicare program. David Heitner, National Producer Number 2098121 #Medicare #MedicareEnrollment #TurningSixtyFive #WorkingPast65 #COBRA #MedicarePenalty #Medicare2026 #MedicareExplained #HeitsBenefits Securities and advisory services offered through Independent Financial Group, LLC (IFG), a Registered Investment Adviser. Member FINRA/SIPC. Heits Benefits Group and IFG are unaffiliated entities. OSJ Branch: 12671 High Bluff Dr. Suite 200. San Diego, CA 92130 IFG Registered Representatives associated with this website may discuss and/or transact business only with residents of the states in which they are properly registered or licensed. Some insurance products are offered outside of the existing Broker Dealer relationship. The information provided is from sources believed to be reliable however, we cannot guarantee or represent that it is accurate or complete. Because situations vary, any information provided on this site is not intended to indicate suitability for any investor. Hyperlinks are provided as a courtesy and should not be deemed as an endorsement. When you link to a third-party website you are leaving our site and assume total responsibility for your use or activity on the third-party sites.