Should You Take COBRA When You Retire Early?

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Should COBRA Be Your Default in Early Retirement?

Keeping your work health insurance after retirement may feel like the easiest choice. But if you’re several years away from Medicare, how does COBRA fit into your longer-term coverage plan?

In this episode, Matt Allen and Aaron Miller explore why COBRA deserves a closer look before becoming your default. We discuss the costs of continuing employer coverage, the alternatives available, and why your health, income, and timeline to Medicare all matter.

You’ll learn about:

  • Why COBRA can cost significantly more than the amount deducted from your paycheck.
  • How COBRA’s typical 18-month duration fits into the gap between retirement and Medicare.
  • Why changes in your health can affect eligibility for medically underwritten plans.
  • How household income and potential ACA tax credits influence your coverage choices.
  • Why provider networks and travel plans deserve attention alongside premiums and deductibles.
  • When upcoming procedures, ongoing care, or deductible progress may make COBRA worth considering.

We also discuss how spouses with different timelines to Medicare may benefit from different coverage strategies, along with the hosts’ perspective on using supplemental coverage to address certain gaps.

The central takeaway: plan for the entire gap to Medicare before choosing COBRA. Comparing your options before leaving work can help you understand the trade-offs, prepare for future transitions, and choose coverage that fits your retirement plans.

About the hosts

Matt Allen brings over a decade of experience helping early retirees bridge the health insurance gap to Medicare. Together with Aaron Miller, he helps make the options and trade-offs easier to understand through Plan Shaman.

Planning to retire before 65?

Plan Shaman provides free health insurance education for individuals and couples preparing for early retirement. Explore your options so you can make a confident decision when the time is right.

Created 10/09/2026