By Daniel Petkevich
Jul 15, 2025
The moment you turn 65, Medicare is expected to pay first. If you stick with COBRA but don’t enroll in Parts A and B, your COBRA plan can refuse most of the bill—leaving you on the hook for what Medicare would’ve paid.
COBRA isn’t “active-employment” coverage, so it doesn’t stop the penalty clock. You have an 8-month Special Enrollment Period that starts the month after employment—or the group plan—ends to sign up for Part B. Miss it and you’ll owe an extra 10 % on your Part B premium for every 12 months you delayed, for life.
If COBRA started before you became Medicare-eligible, the employer can end your COBRA as soon as you sign up for Part A and B. Your spouse and dependents may stay on COBRA (up to 36 months), but your own coverage usually terminates.
Some COBRA plans offer “creditable” prescription coverage—others don’t. Go more than 63 days without creditable drug coverage after becoming Medicare-eligible and you’ll face a Part D penalty (1 % of the national base premium for every month you delayed). Always ask the plan for its annual “creditable-coverage” notice.
Your six-month, one-time Medigap Open Enrollment Period starts when you take Part B. If you delay Part B while lounging on COBRA and your health changes, you may be denied a Medigap policy—or charged more—when you finally apply.
Most people pay the full employer premium—often $600-plus per month—while Medicare Part B runs about $185/month in 2025, and many Medigap Plan G quotes fall below $250. The math rarely favors staying on COBRA once Medicare is available. (Compare your exact numbers to be sure.)
COBRA is great as a short bridge before 65, but once Medicare calls, hanging on to COBRA can leave you with denied claims, lifelong penalties, and higher premiums. Enroll in Medicare on time and consider Medigap or a Medicare Advantage plan for complete, penalty-free coverage.
Our licensed Medicare advocates can walk you through the timelines and run side-by-side cost comparisons—no cost, no pressure. Call 888-376-2028 today.
How Your Employer Insurance and Medicare Work Together
Sep 27, 2022
How to Enroll in Social Security
Apr 28, 2023
Do I Need Medicare If My Spouse Has Insurance?
Dec 19, 2022
Does Medicare Cover Zilretta?
Nov 28, 2022
Does Medicare Cover Hypnotherapy?
Nov 22, 2022
Does Medicare Cover Light Therapy for Psoriasis?
Jan 17, 2023
Does Medicare Cover LVAD Surgery?
Nov 30, 2022
Is Vitrectomy Surgery Covered by Medicare?
Dec 2, 2022
Does Medicare Cover TENS Units?
Nov 23, 2022
Does Medicare Cover Mental Health?
Oct 12, 2022
Does Medicare Cover Krystexxa?
Nov 18, 2022
13 Best Ways for Seniors to Stay Active in Jacksonville
Mar 3, 2023
15 Best Ways for Seniors to Stay Active in Denver
Mar 9, 2023
Health Savings Accounts (HSAs) and Medicare
Jan 24, 2024
What's the Deal with Flex Cards?
Dec 15, 2022
Does Medicare Require a Referral for Audiology Exams?
Nov 22, 2022
How Do Medigap Premiums Vary?
Apr 12, 2023
What People Don't Realize About Medicare
Mar 27, 2023
10 Top Medicare Supplement (Medigap) Companies for 2025
13 Best Ways for Seniors to Stay Active in Columbus
13 Best Ways for Seniors to Stay Active in Phoenix
14 Best Ways for Seniors to Stay Active in Seattle
2024 Fair Square Client Retention and Satisfaction Report
2025 Medicare Price Changes
Can I Laminate My Medicare Card?
Can Medicare Advantage Plans Deny Coverage for Pre-Existing Conditions?
Costco Pharmacy Partners with Fair Square
Do All Hospitals Accept Medicare Advantage Plans?
Do You Need Books on Medicare?
Does Medicare Cover a Spinal Cord Stimulator?
Does Medicare Cover an FMT?
Does Medicare Cover Cataract Surgery?
Does Medicare Cover Compounded Medications?
Does Medicare Cover COVID Tests?
Does Medicare Cover ESRD Treatments?
Does Medicare Cover Hoarding Cleanup?
Does Medicare Cover Home Heart Monitors?
Does Medicare cover Hyoscyamine?
Does Medicare Cover Inqovi?
Does Medicare Cover Iovera Treatment?
Does Medicare Cover Jakafi?
Does Medicare Cover Ketamine Infusion for Depression?
Does Medicare Cover Macular Degeneration?
Does Medicare Cover Mouth Guards for Sleep Apnea?
Does Medicare Cover Nuedexta?
Does Medicare Cover Oxybutynin?
Does Medicare Cover Ozempic?
Does Medicare Cover Physicals & Blood Work?
Does Medicare Cover PTNS?
Does Medicare Cover RSV Vaccines?
Does Medicare Cover Shock Wave Therapy for Plantar Fasciitis?
Does Medicare Cover SI Joint Fusion?
Does Medicare Cover the Urolift Procedure?
Does Medicare Cover the WATCHMAN Procedure?
Does Medicare Cover Tymlos?
Does Medicare Cover Urodynamic Testing?
Does Medicare Cover Xiafaxan?
Does Medicare Pay for Bunion Surgery?
Does Medicare Pay for Funeral Expenses?
Does Medicare pay for Opdivo?
Does Medicare Pay for Varicose Vein Treatment?
Does Retiring at Age 62 Make Me Eligible for Medicare?
Estimating Prescription Drug Costs
Fair Square Bulletin: We're Revolutionizing Medicare
Finding the Best Dental Plans for Seniors
Finding the Best Vision Plans for Seniors
How Are Medicare Star Ratings Determined?
How Can I Get a Replacement Medicare Card?
How Do I Sign up for Medicare? A Simple How-To Guide For You
How is Medicare Changing in 2025?
How Medicare Costs Can Pile Up
How Much Does Medicare Part A Cost in 2025?
How Much Does Trelegy Cost with Medicare?
How Often Can I Change Medicare Plans?
How to Become a Medicare Agent
How to Compare Medigap Plans in 2025
How to Deduct Medicare Expenses from Your Taxes
Is HIFU Covered by Medicare?
Is the Shingles Vaccine Covered by Medicare?
Medicare Savings Programs in Kansas
Medigap Plan N vs. Plan G — Which One Fits You in 2025?
Should You Work With A Remote Medicare Agent?
The Easiest Call You'll Ever Make
Welcome to Fair Square's First Newsletter
What Happens to Unused Medicare Set-Aside Funds?
What Is the Medicare Birthday Rule in Nevada?
What to Do When Your Doctor Doesn't Take Medicare
What You Need to Know About Creditable Coverage
What's the Difference Between HMO and PPO Plans?
Why You Should Keep Your Medigap Plan
Get the Fair Square Bulletin
Medicare savings tips, helpful guides, and more.
Virgil Insurance Agency, LLC (DBA Fair Square Medicare) and www.fairsquaremedicare.com are privately owned and operated by Help Button Inc. Medicare supplement insurance plans are not connected with or endorsed by the U.S. government or the federal Medicare program. This is a solicitation of insurance. A licensed agent/producer may contact you. Medicare Supplement insurance is available to those age 65 and older enrolled in Medicare Parts A and B and, in some states, to those under age 65 eligible for Medicare due to disability or End-Stage Renal disease. Virgil Insurance Agency is a licensed and certified representative of Medicare Advantage HMO, HMO SNP, PPO, PPO SNP and PFFS organizations and stand-alone PDP prescription drug plans. Each of the organizations we represent has a Medicare contract. Enrollment in any plan depends on contract renewal. The plans we represent do not discriminate on the basis of race, color, national origin, age, disability, or sex. Plan availability varies by region and state. For a complete list of available plans please contact 1-800-MEDICARE (TTY users should call 1-877-486-2048), 24 hours a day/7 days a week or consult www.medicare.gov. © 2025 Help Button Inc
We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.
MULTIPLAN_FairSquareMedicare_01062022_M
Fair Square Medicare