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Medicare Enrollment Checklist

This checklist will help ensure you complete the necessary steps to activate and coordinate your Medicare benefits properly. If you would like to speak with a Licensed Insurance Agent please call 1-833-505-5210. TTY Call 711

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Your Medicare Enrollment Checklist: A Step-by-Step Guide

βœ… Step 1: Confirm Your Medicare Part A Enrollment

 Most individuals are automatically enrolled in Original Medicare Part A (Hospital Insurance) when turning 65 if already receiving Social Security benefits.

βœ” Confirm your enrollment
βœ” Verify your mailing address
βœ” Watch for your red, white, and blue Medicare card

Call:
πŸ“ž 1-800-MEDICARE (1-800-633-4227)
OR
πŸ“ž Social Security: 1-800-772-1213

Medicare is administered by the Centers for Medicare & Medicaid Services.

βœ… Step 2: If You Are Still Working or Planning to Retire

 Before making any changes:

βœ” Speak with your employer’s benefits administrator
βœ” Confirm how your employer coverage coordinates with Medicare
βœ” Ask if your coverage is considered β€œcreditable”
βœ” Confirm when your employer coverage ends
βœ” Request documentation showing your coverage dates

This step helps prevent late enrollment penalties.

βœ… Step 3: Enroll in Medicare Part B (If Retiring)

 If you are retiring and losing employer coverage, you must enroll in Medicare Part B (Medical Insurance) to avoid penalties.

Call to enroll:

πŸ“ž 1-800-MEDICARE OR
πŸ“ž Social Security: 1-800-772-1213

Have ready:

  • Your Social Security number
  • Employer coverage termination date

βœ… Step 4: Decide How You Want to Receive Your Medicare Coverage

You generally have three structured paths to consider:

Option A: Original Medicare Only (Part A & Part B)

βœ” Coverage managed by the federal government
βœ” No provider network restrictions (accepts providers who take Medicare)
βœ” You are responsible for deductibles, coinsurance, and cost-sharing

This option does not include prescription drug coverage.
You may want to consider adding a Part D plan.

Option B: Original Medicare + Medicare Supplement (Medigap)

βœ” Keeps Original Medicare (Part A & Part B)
βœ” Adds a Medicare Supplement (Medigap) policy to help cover out-of-pocket costs
βœ” Typically allows nationwide provider access (no network restrictions)
βœ” Requires a separate Part D prescription drug plan

Medigap policies are standardized and designed to help reduce financial exposure such as deductibles and coinsurance.

This option is often selected by individuals who prioritize predictable costs and provider flexibility.

Option C: Medicare Advantage (Part C)

βœ” Combines Part A & Part B
βœ” Often includes prescription drug coverage
βœ” May include additional benefits (such as dental, vision, hearing, etc.)
βœ” May use provider networks
βœ” Has plan-specific cost structures

Medicare Advantage plans are offered by private insurance companies approved by the Centers for Medicare & Medicaid Services.

Important Reminder

Each option has different:

  • Cost structures
  • Provider access rules
  • Prescription coverage requirements
  • Out-of-pocket exposure
     

A licensed consultation can help determine which structure aligns best with your healthcare needs, budget, and provider preferences.

βœ… Step 5: Review Prescription Drug Coverage

 βœ” Make a list of your medications
βœ” Confirm dosage and frequency
βœ” Check if they are covered under your selected plan
βœ” Verify pharmacy network participation

Prescription coverage varies by plan.

βœ… Step 6: Understand Enrollment Deadlines

 Be aware of your enrollment window:

  • Initial Enrollment Period (7-month window around your 65th birthday)
  • Annual Enrollment Period (October 15 – December 7)
  • Special Enrollment Period (if eligible)

Missing deadlines may result in permanent penalties.

Frequently Asked Questions

At Heritage Assurance Insurance, we specialize in a wide range of Medicare insurance products designed to serve individuals, families, and seniors with care, clarity, and confidence. Please reach us at info@heritage-assurance.com if you cannot find an answer to your question. 

Medicare Part A

Hospital insurance that typically covers:

  • Inpatient hospital stays
  • Skilled nursing facility care
  • Hospice
  • Limited home health services
     

Medicare Part B

Medical insurance that covers:

  • Doctor visits 
  • Outpatient care
  • Preventive services
  • Durable medical equipment
     

Medicare Part C (Medicare Advantage)

Offered by private insurance companies approved by Medicare. These plans bundle Part A and Part B and often include additional benefits.


Medicare Part D

Prescription drug coverage offered through private insurers approved by Medicare.


Original Medicare (Part A & Part B):

  • Coverage managed by the federal government
  • May require a separate Part D plan for prescriptions
  • May require a Medigap policy for out-of-pocket cost support
     

Medicare Advantage (Part C):

  • Administered by private insurers
  • Often includes prescription coverage
  • May include additional benefits such as dental or vision
  • May use provider networks

The option that meets your needs depends on healthcare needs, provider preferences, and budget considerations. 


Initial Enrollment Period (IEP)

Begins 3 months before your 65th birthday, includes your birthday month, and ends 3 months after.


Annual Enrollment Period (AEP)

October 15 – December 7 each year. Changes take effect January 1.


Special Enrollment Period (SEP)

May apply if you experience certain life events (such as losing employer coverage). 


 


If you are already receiving Social Security benefits, you may be automatically enrolled in Part A and Part B.


If you are still working and covered by employer insurance, your enrollment timing may differ. It’s important to review your situation carefully to avoid late enrollment penalties.


Medigap policies are sold by private companies to help cover out-of-pocket costs such as:

  • Copayments
  • Coinsurance
  • Deductibles

Medigap works alongside Original Medicare and does not replace it.


Prescription drugs are generally covered under:

  • Medicare Part D offered through private insurers approved by Medicare 
  • Most Medicare Advantage plans

Each plan has its own formulary (list of covered medications), so reviewing drug coverage annually is important.  


Coverage depends on:

  • Whether you have Original Medicare or Medicare Advantage
  • Whether your provider accepts Medicare
  • Whether your plan uses a network 

Heritage Assurance help clients quickly confirm doctor participation and prescription coverage during appointments.


 Yes. If you delay enrollment in:

  • Part B 
  • Part D

You may face lifetime penalties unless you qualify for a Special Enrollment Period.


Costs vary based on:

  • Income level
  • Coverage choices
  • Whether you add supplemental coverage
  • Prescription needs 

Most people receive Part A without a premium if they meet work history requirements. Part B and Part D typically have monthly premiums.


Yes, for Medicare Advantage (Part C) and Prescription Drug Plans can change during:

  • Annual Enrollment Period (AEP)
  • Medicare Advantage Open Enrollment Period (January 1 – March 31)
  • Special Enrollment Periods (if eligible)

Plan reviews annually are strongly recommended.


If you are in a Medicare Supplement plan (Medigap), you may change your plan anytime.


We provide structured, compliance-focused consultations to:

  • Compare plan options
  • Review provider access
  • Evaluate prescription coverage
  • Explain cost exposure
  • Support enrollment decisions

Our goal is clarity β€” not confusion.


Guiding You with Care

Let Us Be Your Forever Insurance Agent

At Heritage Assurance Insurance, we are dedicated to providing our clients with the highest quality of health coverage at its lowest cost with options that meets their specific needs.  We provide structured, compliance-focused consultations to:

  • Compare plan options
  • Review provider access
  • Evaluate prescription coverage
  • Explain cost exposure
  • Support enrollment decisions

Our goal is clarity β€” not confusion.

Copyright Β© 2026 Heritage Assurance - All Rights Reserved.


We do not offer every plan available in your area. Currently we represent 6 organizations which offer products in your area. Please contact Medicare.gov, 1-800-MEDICARE (1-800-633-4227), or your local State Health Insurance Program (SHIP) to get information on all of your options.  


 The Medicare plans represented are PDP, HMO, PPO or PFFS plans with a Medicare contract. Enrollment in plans depends on contract renewal. Enrollment in a plan may be limited to certain times. Eligibility may require a Special or Medicare Initial Enrollment Period. Heritage Assurance and Medicare supplement insurance plans are not connected with or endorsed by the U.S. government or the federal Medicare program. 

 

Benefits shown are for the 2026 plan year. Not all plans offer all benefits mentioned. Benefits may vary by carrier and location. Deductibles, copays, and coinsurance may apply. Limitations and exclusions may apply. $0 premium plans are not available in all areas. You must continue to pay your Part B Premium. 

Part B Premium Reduction is not available with all plans. Availability varies by carrier and location. Actual Part B premium reduction could be lower.


 By initiating a chat or scheduling a call you are agreeing to be contacted by a licensed sales agent by email, text message, or phone call to discuss information about Medicare insurance plans. This is a solicitation for insurance. Standard messaging rates may apply. 

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