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  • More
    • Home
    • About
    • Fees
    • Schedule Intro Meeting
    • Strategic Directions
    • Curriculum
      • Class Catalog
      • (01) Investing in Fitness
      • (02) Legal Documents
      • (03) Social Security
      • (04) TIPS Ladder
      • (05) Investment Portfolio
      • (06) Taxes in Retirement
      • (07) Spending Capacity
      • (08) Medicare Enrollment
      • (W1) Roth Conversions
    • Recommended Resources
    • Intro Videos
    • Focus Areas

  • Home
  • About
  • Fees
  • Schedule Intro Meeting
  • Strategic Directions
  • Curriculum
    • Class Catalog
    • (01) Investing in Fitness
    • (02) Legal Documents
    • (03) Social Security
    • (04) TIPS Ladder
    • (05) Investment Portfolio
    • (06) Taxes in Retirement
    • (07) Spending Capacity
    • (08) Medicare Enrollment
    • (W1) Roth Conversions
  • Recommended Resources
  • Intro Videos
  • Focus Areas

Medicare Enrollment

Videos
Medicare Enrollment Basics (13:56)Medicare Enrollment Example (13:21)

Initial Enrollment Period at 65

Choosing Medicare Advantage (Part C)

Initial Enrollment Period at 65

  • 7-month Initial Enrollment Period surrounding the 65th birthday 
  • Begins 3 months before the birthday month
  • Includes the birthday month
  • Ends 3 months after the birthday month
  • Tip Enroll in one of the 3 months before the birthday month so coverage starts on the first of the birthday month
  • Special case If the birthday is on the 1st of the month, Medicare and Social Security considers this as turning 65 the previous month
  • Start enrollment on ssa.gov 

Delayed Medicare

Choosing Medicare Advantage (Part C)

Initial Enrollment Period at 65

  • Working past 65 with employer coverage Medicare enrollment can generally be delayed without penalty when there is creditable group health coverage from an employer (employee or spouse)
  • Special Enrollment Period (SEP) After employer coverage ends, an 8-month window opens to enroll in Part B penalty-free. Missing this window can trigger a lifetime Part B late enrollment penalty
  • In many situations, Original Medicare with Plan G and a Part D plan delivers coverage that's as good as or better than what most people had during their working years through an employer
  • Before delaying Medicare, know the rules

Choosing Medicare Advantage (Part C)

Choosing Medicare Advantage (Part C)

Choosing Original Medicare with Medigap

  • Premiums are typically lower — some plans have $0 monthly premium
  • Bundles Part D drug coverage (Original Medicare does not)
  • Often includes extra benefits: dental, vision, hearing, gym memberships, OTC allowances
  • Annual out-of-pocket maximum (Original Medicare has none without Medigap)
  • Familiar HMO or PPO structure
  • Heavy advertising and broker marketing make MA the most visible option

Choosing Original Medicare with Medigap

Choosing Original Medicare with Medigap

Choosing Original Medicare with Medigap

  • Accepted by any provider that accepts Medicare — the vast majority nationally
  • Better for frequent travelers (no network restrictions)
  • Far fewer prior authorization requirements compared to Medicare Advantage
  • Predictable out-of-pocket costs with Plan G (only the annual Part B deductible)
  • Stable, federally standardized benefits that don't change year to year

Original Medicare protections and rules

Choosing Original Medicare with Medigap

Original Medicare protections and rules

  • Medigap Open Enrollment 6-month window starting when enrolled in Part B at 65, during which carriers cannot deny coverage or charge more based on health
  • Plan G coverage covers the 20% Original Medicare doesn't (except the annual Part B deductible)
  • Continuous coverage as long as Original Medicare is maintained, Medigap continues without re-underwriting
  • Limited switching protections exceptions exist where someone can move from Medicare Advantage back to Original Medicare with guaranteed Medigap issue (plan discontinued, moved out of service area, first-year trial right)
  • State-specific rules apply some states (like California's birthday rule) offer additional protections — worth researching locally

Copyright © 2026  Ty Rollins - All Rights Reserved.

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