Still Working Past 65? Find Out What Medicare Steps You May Need to Take
Answer a few quick questions to see whether you may be able to delay Part B, whether you should review Medicare before retiring, and what to look at before your work coverage ends.
- Takes about 60 seconds
- Plain-English results
- No obligation
Built to help people retiring at 65, 66, or 67 understand their next Medicare step.
Your Medicare Deadline Check
Answer each question — then see your personalized results below.
Which best describes you right now?
What kind of health coverage do you have right now?
About how many employees does the employer have?
(This can affect your Medicare timing.)
Which of these apply to you? (Check all that apply)
When do you expect to retire or lose your current coverage?
Are you currently contributing to a Health Savings Account (HSA)?
When you move into Medicare, what matters most to you?
What to review next
One quick question before we continue
This helps us make sure the follow-up is as useful as possible for you.
What would you like help with next?
Thank You — Your Information Has Been Received
A licensed agent from We Know Medicare will review your information and follow up based on the Medicare timeline you shared. If you prefer to speak sooner, you can call us directly.
Call Us: 920-545-4884Our team typically responds within one business day.
Why people use this Medicare checker
You're not alone — these are some of the most common situations we see.
Still Working Past 65
Wondering if you really need to sign up now — or whether your job coverage is enough for the moment.
Retiring Soon
Getting closer to your retirement date and want to know which Medicare steps to take, and when.
Unsure Whether to Enroll Yet
Confused by conflicting information about deadlines, penalties, and your options. Looking for plain-English clarity.
Common questions
Not necessarily. If you're already drawing Social Security when you turn 65, you may be enrolled in Parts A and B automatically. If you're not receiving Social Security yet, you may need to sign up on your own — usually through Social Security during your Initial Enrollment Period. This checker can help you think through where you likely stand.
In many cases, yes — if you have active coverage through your own or your spouse's employer, and that employer has 20 or more employees, you may be able to delay Part B without a late penalty. The employer size detail matters here. This checker is designed to help flag whether your situation may allow for a delay, and what to look at more closely.
Generally no. COBRA is continuation coverage that you pay for yourself after leaving employment. For Medicare purposes, it is typically not treated the same as active employer coverage. If you're on COBRA and approaching 65, your Medicare enrollment timing may be different than if you had active employer coverage. This is worth reviewing closely with a licensed agent.
Yes — and this is worth reviewing carefully. Marketplace and ACA coverage is different from active employer coverage, so Medicare timing may need a closer look. Once you become eligible for Medicare, your Marketplace plan may change in important ways, and you may want to review how the two interact before your 65th birthday. A licensed agent can help you sort through the timing.
Yes — that's part of why we ask about your coverage preferences. After we review your timeline together, a licensed agent can walk you through how Medicare Supplement (Medigap) plans and Medicare Advantage plans differ, and which approach may fit your priorities. There's no pressure to choose anything — just a clear, personalized comparison.
