Medicare Enrollment Mistakes to Avoid
Medicare enrollment mistakes to avoid can save you thousands and preserve your healthcare options. A missed deadline or wrong plan choice can lead to penalties, denied coverage, or expensive surprises. At Diversified Insurance Brokers, we guide you through every enrollment step to help you avoid costly errors and secure the plan that meets your needs.
Avoid Costly Medicare Enrollment Mistakes
Let us help you navigate enrollment periods and avoid penalties so you can focus on healthcare, not paperwork.
Common Medicare Enrollment Mistakes
- Missing Initial Enrollment Period (IEP): You have 7 months around your 65th birthday—signing up late can result in permanent Part B penalties.
- Skipping Part D or Medigap during guaranteed issue: Missing coverage when first eligible may disqualify you from affordable plans later.
- Choosing a Medicare Advantage plan without checking provider networks: If your doctors or specialists aren’t in-network, you may pay more or lose access to care.
- Underestimating prescription drug needs: Choosing the wrong Part D formulary can lead to high out-of-pocket costs for expensive medications.
- Thinking costs end at zero-premium Advantage plans: These can include high copays or limited benefits—especially if you have chronic health needs.
Compare Plans Easily and Avoid Mistakes
Use our Medicare comparison calculator to evaluate plan premiums, networks, and drug coverage side by side—quickly and clearly.
Planning Tips to Prevent Enrollment Errors
- Set alerts for enrollment periods: Mark your Initial, Annual, and Special Enrollment Period windows on your calendar.
- Get help if your coverage lags: If you were late enrolling due to employer coverage or disability, repurpose documentation to avoid penalties.
- Review each year during Open Enrollment: Plan benefits, networks, and drug formularies change every year—review and update as needed.
- Don’t assume zero premium means “best value”: Check the full total cost—deductibles, copays, pharmacy access, and included services.
Case Example
Mark delayed Part B enrollment because he was still covered by an employer plan, but never reported this during his Medicare window—resulting in a Part B late penalty and Medigap underwriting hassle. We helped him re-enroll using Special Enrollment Period documentation and prevented a premium increase from becoming permanent.
Useful Resources
- Medicare Supplement Coverage for Cancer Treatment
- How to Choose the Best Medicare Plan
- Medicare Plans with Dental & Vision Coverage
Why Work With Diversified Insurance Brokers?
Since 1980, we’ve made Medicare enrollment easy and error-free for our clients. Our checklists, reminders, and support help you avoid costly missteps—so you can focus on your health. Learn more about why families trust us.
Let’s Avoid Costly Medicare Mistakes Together
Book a free consultation with Tonia to ensure your Medicare enrollment is complete, correct, and optimized for your needs.
FAQs: Medicare Enrollment Mistakes to Avoid
What’s the most common Medicare enrollment mistake?
Missing your Initial Enrollment Period (IEP). If you don’t have qualifying coverage and you delay, you can face lifelong late-enrollment penalties and gaps in coverage.
When is my Initial Enrollment Period (IEP)?
It’s a 7-month window: the 3 months before your 65th birthday month, your birthday month, and the 3 months after. Enrolling early helps avoid delays in coverage start dates.
Can I delay Part B without a penalty if I’m still working?
Yes, if you have creditable employer coverage from an employer with 20+ employees (for your own or spouse’s active employment). Otherwise, delaying Part B can trigger penalties.
Is COBRA or retiree coverage “creditable” for delaying Part B?
Usually no for Part B. Relying on COBRA/retiree coverage to delay Part B commonly leads to penalties and a gap until the next enrollment period. Verify Part D creditable status separately for drug coverage.
What about Part D late-enrollment penalties?
If you go 63+ days without creditable drug coverage after your IEP, you can owe a permanent Part D penalty added to your premium. Keep continuous creditable drug coverage to avoid it.
How does employer size affect my decision to enroll at 65?
With employers under 20 employees, Medicare is usually primary—so you generally should enroll in Part A and Part B at 65. With 20+ employees, you may delay Part B if the group plan is creditable.
Can I keep contributing to an HSA after I start Medicare?
No. Once Part A (or any part of Medicare) starts, HSA contributions must stop. Part A can retroactively start up to 6 months (not earlier than your eligibility), so plan contributions carefully.
What’s the risk of skipping Medigap during my guaranteed-issue window?
If you want Original Medicare + Medigap, your best time to buy Medigap is the 6-month window starting with your Part B effective date. After that, you may face medical underwriting or denial in many states.
Should I verify my doctors and drugs before choosing a plan?
Always. Make sure your doctors are in-network for Medicare Advantage and that your medications are on the plan formulary (and check tiers/pharmacies). For Medigap, confirm the providers accept Medicare.
Do I need to review my coverage every year?
Yes. Formularies, premiums, networks, and benefits change annually. Use the Annual Enrollment Period (Oct 15–Dec 7) to switch if a different plan offers better value for the coming year.
What’s the difference between Medicare Advantage MOOP and Original Medicare?
Medicare Advantage plans have an in-network maximum out-of-pocket (MOOP). Original Medicare has no MOOP; many beneficiaries add a Medigap policy to limit out-of-pocket costs.
What if I missed my IEP—when can I enroll?
You may qualify for a Special Enrollment Period (SEP) if you had creditable coverage. Otherwise, you can enroll during the General Enrollment Period (Jan 1–Mar 31), with coverage typically starting the month after you enroll and potential penalties applied.
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