Medicare Annual Enrollment Period: Your Complete Checklist

Medicare’s Annual Enrollment Period runs from October 15 through December 7, and it’s your only chance to make changes to your coverage for next year. Don’t sleepwalk through this decision – even if you love your current plan, things change, and so might your needs.

Why This Window Matters

Medicare plans change every year. Your current plan might have dropped your doctor, increased drug costs, or eliminated benefits you rely on. Meanwhile, new plans could offer better coverage or significant savings you’re missing. Beneficiaries who don’t review their plans annually often pay hundreds more than necessary.

 

Man using iPad

Step 1: Gather Your Information

Before comparing plans, collect what you need to make informed decisions:

  • Current Medicare card and plan materials
  • Complete list of medications with dosages
  • Contact information for all your healthcare providers
  • Recent medical bills and pharmacy receipts
  • Your preferred pharmacy information

Take stock of any health changes over the past year. New conditions, medications, or planned procedures all affect which plan works best for you.

Step 2: Review Your Current Coverage

Don’t assume your plan works the same way next year. Check your Annual Notice of Change letter carefully.

For Prescription Drug Coverage (Part D) Verify all your medications are still covered and haven’t moved to higher-cost tiers. Use Medicare.gov’s Plan Finder to calculate your total annual drug costs, including deductibles and copays – not just monthly premiums.

For Medicare Advantage Plans Confirm your doctors and hospitals are in-network. Review changes to copays, deductibles, and extra benefits like dental or vision coverage. Sometimes small premium increases hide significant cost increases elsewhere.

Step 3: Shop and Compare Smartly

Here’s where people often go wrong: focusing only on monthly premiums instead of total costs.

Use Official Tools Medicare.gov’s Plan Finder gives you personalized cost estimates when you enter your medications. Consider calling your State Health Insurance Assistance Program (SHIP) for free, unbiased help.

What Really Matters

  • Total estimated annual costs (premiums + out-of-pocket expenses)
  • Provider network quality and stability
  • Prescription drug coverage for your specific medications
  • Plan star ratings (1-5 scale for quality and performance)
  • Extra benefits that add real value to your situation

Step 4: Make Your Decision

Once you’ve done your homework, don’t wait. The December 7 deadline is firm, with no extensions.

How to Enroll

  • Online at Medicare.gov (fastest option)
  • Call 1-800-MEDICARE
  • Contact plans directly

 

The Bottom Line

This isn’t just paperwork – it’s your opportunity to potentially save money and improve your coverage. Even if you stick with your current plan, you’ll have confidence you made an informed choice.

Set aside a few hours in the next couple of weeks to review your options. Your future self will thank you when you’re not stuck with a plan that doesn’t meet your needs or costs more than necessary.

Get Help If You Need It

Free assistance is available:

  • Medicare.gov for plan comparisons
  • 1-800-MEDICARE for official guidance
  • SHIP programs for local, unbiased counseling

Remember: Your new coverage starts January 1, but you must enroll by December 7. Don’t let another year pass wondering if you’re getting the best value from Medicare. Take control now and make your coverage work for you.


This information is for educational purposes only and should not be considered personalized insurance advice. Always consult with qualified insurance professionals or Medicare directly for guidance specific to your situation.

Page Last Updated On: September 22, 2025
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Tom Cunniffe

Tom Cunniffe

Director of Operations 

Tom Cunniffe comes to eternalHealth with over 20 years of healthcare operations’ experience, having held leadership positions in Call Center, Enrollment, Credentialing, UAT and Reimbursement teams. Tom has worked with Medicaid, Commercial and Medicare lines of business and has consistently built teams who are metrics driven with proven successful outcomes. Making sure our business strives for an efficient, best-in-class customer experience is at the center of Tom’s philosophy.

Tom has a bachelor’s degree from Fordham University and a master’s in business administration from University of Massachusetts at Amherst.

Tom Lawless

Tom Lawless

Chief Financial Officer

Tom Lawless has spent the past 20+ years building, sustaining, and growing new healthcare-related programs that balance fiscal responsibility & prudence with creativity & innovation, focusing on models of care that are novel, person-centered, and improve the social welfare of those who are served. He is very excited to continue doing so in his role as the Chief Financial Officer of eternalHealth.

Tom comes to eternalHealth from a not-for-profit, member-centric, health insurance cooperative. He helped the company continuously strive toward its dual goals of thriving financially, while keeping members at the very epicenter of its mission and service model. While there, Tom also spearheaded the creation of a brand new private, charitable foundation, which will be meaningfully giving back to those in need in the surrounding communities for years to come. Previously, Tom worked in the finance department of a successful hospice that provided high-quality care to persons experiencing their unique and poignant end-of-life journeys, assuring that the appropriate financing was always available. Tom’s career began as a civil servant in the Wisconsin Medicaid program, where he helped to create a program that expanded the institutional entitlement to care into home and community-based settings. Starting with only a blueprint in hand, the program now serves more than 57,000 frail elders and disabled adults and is considered a national model. Growing into a senior leadership role, Tom was a key architect of an innovative financing model, through which the public and private sectors successfully collaborated to better the lives of persons in great need.

Tom holds undergraduate and graduate degrees from the University of Chicago, with additional graduate work in economics completed at the University Wisconsin-Madison.

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