Written by Michael LaPick
Healthcare Writer
We aim to help you make informed healthcare decisions. While this post may contain links to lead generation forms, this won’t influence our writing. We follow strict editorial standards to give you the most accurate and unbiased information.
Key Takeaways
- Medicare decisions are easier when you start conversations early and understand enrollment periods.
- Comparing plans means looking at more than premiums—check doctors, drug coverage, and annual costs.
- Outside of Original Medicare (Parts A & B), additional coverage options include Medicare Advantage, Medicare Supplement (Medigap), and Part D drug plans.
- Caregivers can help parents avoid common pitfalls like sticking with outdated plans or choosing based solely on advertising.
- Licensed Medicare agents and comparison tools can make reviewing options faster and easier.
OverviewÂ
Many adults face a unique challenge: planning their own retirement while helping aging parents navigate Medicare. With changing rules, shifting drug formularies, and multiple plan types, it’s common to wonder not just how to help your parents choose a Medicare plan—but also when you can sign up for Medicare yourself.
A little support can make a big difference, helping your loved ones avoid costly mistakes and overlooked benefits. This guide breaks the process into simple steps, highlights what to compare, and explains who can help you choose a Medicare plan if you need expert assistance.
You don’t need to be an insurance expert to help. By understanding key enrollment periods and plan options, you can guide your parents toward coverage that truly fits their health and budget.
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How to Start the Medicare Conversation
Talking about healthcare and finances with your parents can be sensitive. But a thoughtful, collaborative approach can make all the difference.
Tips for a productive discussion
- Ask open-ended questions. “How do you feel about your current plan?” or “Have your health needs changed this year?”
- Listen for concerns. Many seniors fear losing their doctor or dealing with unexpected drug costs.
- Review medications and providers. Make a shared list to reference during comparisons.
- Discuss budget comfort levels. Some parents prefer predictable costs (Medicare Supplement insurance, also known as Medigap), while others want low premiums (Medicare Advantage).
Starting early, well before major enrollment periods, helps you avoid rushed or emotional decisions.
Key Enrollment Periods to Know
One of the most common questions caregivers ask is: “When can I sign up for Medicare?” Understanding these timelines helps you guide your parents and plan for yourself.
Medicare Enrollment Windows
| Enrollment Period | What It Covers | When It Happens |
| Initial Enrollment Period (IEP) | First-time enrollment in Parts A & B | 7-month window around turning 65 |
| Annual Enrollment Period (AEP) | Change Medicare Advantage or Part D plans | Oct 15 – Dec 7 annually |
| Medicare Advantage Open Enrollment (MA-OEP) | Switch Medicare Advantage plans | Jan 1 – Mar 31 annually |
| Special Enrollment Periods (SEPs) | Triggered by moves, loss of coverage, or qualifying events | Varies |
Understanding these windows ensures your loved one doesn’t miss an opportunity to adjust coverage or lower costs.
Know Your Plan Options Outside of Original Medicare
Original Medicare covers hospital and medical services, but it leaves gaps—like prescription drug coverage, and routine dental, hearing, vision, and out-of-pocket limits. Our 2026 guide to Medicare plans can help your parents or loved ones with a clearer picture of what they may need. Â
Medicare Advantage (Part C)
Medicare Advantage (Part C) combines hospital, medical, and often prescription drug coverage into one package. These plans may also include routine dental, hearing and vision. If you’re helping a parent compare options, exploring the best Medicare Advantage companies may be a helpful starting point.
Medicare Supplement Insurance (Medigap)
Medigap helps cover deductibles and other out-of-pocket costs that Original Medicare doesn’t.Â
You’ll see there are a variety of plans, each identified by a letter: A, B, C, D, F, G, K, L, M, and N.Â
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Medicare Supplement Plans Comparison Chart
| Medigap Benefits | Plan A | Plan B | Plan C | Plan D | Plan F* | Plan G* | Plan K | Plan L | Plan M | Plan N* |
| Part A coinsurance & hospital costs (up to 365 days after Medicare benefits used) | âś“ | âś“ | âś“ | âś“ | âś“ | âś“ | âś“ | âś“ | âś“ | âś“ |
| Part B coinsurance or copayment | âś“ | âś“ | âś“ | âś“ | âś“ | âś“ | 50% | 75% | âś“ | âś“*** |
| First 3 pints of blood | âś“ | âś“ | âś“ | âś“ | âś“ | âś“ | 50% | 75% | âś“ | âś“ |
| Part A hospice care coinsurance or copayment | âś“ | âś“ | âś“ | âś“ | âś“ | âś“ | 50% | 75% | âś“ | âś“ |
| Skilled nursing facility care coinsurance | X | X | âś“ | âś“ | âś“ | âś“ | 50% | 75% | âś“ | âś“ |
| Part A deductible | X | âś“ | âś“ | âś“ | âś“ | âś“ | 50% | 75% | 50% | âś“ |
| Part B deductible | X | X | âś“ | X | âś“ | X | X | X | X | X |
| Part B excess charges | X | X | X | X | âś“ | âś“ | X | X | X | X |
| Foreign travel emergency (up to plan limits) | X | X | 80% | 80% | 80% | 80% | X | X | 80% | 80% |
| Out-of-pocket limit** | N/A | N/A | N/A | N/A | N/A | N/A | $7,220 (2025) | $3,610 (2025) | N/A | N/A |
Source: Medicare.gov
If you want to understand which insurers perform well, see our guide to the best Medicare Supplement insurance companies.
Medicare Part D (Prescription Drug Plans)
These drug plans differ in formularies, premiums, and copay tiers. Compare plans based on your parents’ prescriptions.
How to Compare Medicare Plans (What Really Matters)
It’s tempting for seniors to choose plans based on the lowest premium—but that rarely leads to the best coverage.
What to Compare
- Provider networks
- Drug formularies
- Total annual cost
- Coverage flexibility
- Extra benefits
You can compare multiple Medicare plans through Healthcare.com’s comparison tools or connect with a licensed Medicare agent anytime.
You can also reference how Medicare Advantage compares to Medigap in our full breakdown.
Common Medicare Mistakes to Avoid
Many older adults unknowingly overpay or lose coverage because of simple misunderstandings. As a caregiver, you can help them sidestep these issues.
Top pitfalls
- Sticking with the same plan year after year
- Choosing a plan based on advertising
- Ignoring drug formulary changes
- Assuming Original Medicare covers everything
A quick yearly review helps your parent stay protected and avoid unnecessary costs.
When to Bring in a Licensed Medicare Agent
If you or your parents feel overwhelmed, get help. A licensed Medicare agent can compare plans, explain differences, and walk you through paperwork.
Shop for a Medicare plan with additional benefits!
Bottom Line
Helping your parents choose the right Medicare plan is one of the most meaningful ways you can support their long-term well-being. By understanding when you can sign up for Medicare, comparing plan types, and using available resources, you can guide your loved ones with clarity and confidence.
Whether they’re choosing between Medicare Advantage and Medigap, weighing top-rated insurers, or exploring how to switch plans, the tools available through Healthcare.com and MedicareGuide.com can make the process far easier.
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