FIRE Healthcare Checklist: Everything to Arrange Before You Retire

Healthcare is the most complex part of early retirement planning — and the most dangerous to leave until the last minute. Lose employer coverage without a plan in place, and you could face a coverage gap, a missed subsidy, or a permanent Medicare penalty.

This is your complete, phase-by-phase healthcare checklist. Work through it in order, and you'll hit your retirement date fully covered, fully informed, and with no surprises.

• Learn what your ACA income target should be Visit healthcare.gov's plan preview tool. Enter your expected retirement income at various levels to see how subsidies change. Identify the MAGI range that gives you the best premium-to-coverage ratio.
• Audit your income sources for MAGI impact List every source of retirement income — Roth withdrawals (don't count), traditional IRA/401k draws (do count), capital gains (do count), Social Security (partially counts). Map out your expected MAGI before you retire.
• Maximize HSA contributions while employed If you're on an HDHP, contribute the family or individual max every year until you leave your employer. These contributions reduce current taxable income and build your healthcare reserve tax-free.
• Start saving medical receipts now If you pay any medical, dental, or vision expenses out of pocket, save every receipt. HSA reimbursements have no deadline — expenses from today can be withdrawn tax-free in 20 years.
• Get major medical procedures done while employed Employer insurance typically offers lower out-of-pocket costs and broader networks. Schedule any elective procedures, dental work, vision correction, or specialist visits before your coverage ends.
• Research ACA plans in your target zip code If you're planning to move, check ACA plan options in your destination state. Premiums and plan availability vary dramatically by location — some areas have excellent, affordable options; others don't.

• Decide between COBRA and ACA for transition coverage If you retire in the first half of the year, COBRA may be worth it to get through a high-income partial year (from your salary). If you retire in November or December, ACA Open Enrollment may time perfectly.
• Understand your Special Enrollment Period Losing employer coverage triggers a 60-day SEP to enroll in an ACA plan. Know when your coverage ends and count 60 days forward — that's your enrollment deadline if you're not using COBRA.
• Check if your spouse's employer plan covers you If your spouse is still working, get specific: what does it cost to add you? Is it an HDHP (HSA-eligible)? Does their employer cover family premiums generously? This may be your best option.
• Budget healthcare costs in your FIRE model Enter realistic healthcare costs in your retirement calculator — not just premiums, but deductibles, copays, dental, and vision. $6,000–$15,000/year per household is a reasonable starting range.
• Research long-term care insurance The earlier you apply for LTC insurance, the cheaper and easier it is to qualify. Ages 55–65 are the sweet spot. Understand what you'd need it for and whether self-insuring (with portfolio assets) is a better alternative.

• Elect COBRA or enroll in ACA — do not have a gap There should be zero days between your employer coverage ending and your new coverage beginning. Even one uninsured day creates legal and financial risk.
• Get a full physical and prescription stock-up Use your employer insurance for a comprehensive physical, blood work, and to fill prescriptions with 90-day supplies before your coverage changes. Continuity matters.
• Roll your HSA if your employer's is mediocre Once you leave your employer, you're free to roll the HSA to a better provider (like Fidelity). You can do one trustee-to-trustee transfer per year without tax implications.
• Verify your ACA plan's network includes your doctors Before finalizing an ACA plan, confirm that your primary care physician, specialists, and any hospitals you use are in-network. This takes 15 minutes and can save thousands.

• Update your ACA income estimate each November Open Enrollment runs November 1 – January 15. Review your expected next-year income and update your application. Under- or over-estimating income affects your monthly subsidy and year-end reconciliation.
• Compare plans annually — don't auto-renew blindly Insurers change premiums, networks, and formularies every year. The plan that was best this year may not be best next year. Spend 30 minutes in October comparing your options.
• Track medical expenses for HSA reimbursement Keep a running log (a simple spreadsheet works) of every medical expense paid out of pocket, with the date, amount, and receipt. This is your future tax-free withdrawal inventory.

• Mark your Medicare enrollment window (3 months before birthday) Your Initial Enrollment Period starts 3 months before your 65th birthday. Begin the process at ssa.gov or medicare.gov at least 2–3 months before your birthday to avoid coverage gaps.
• Choose: Original Medicare + Medigap vs Medicare Advantage This is a major decision. Original Medicare + Medigap Plan G gives you predictable costs and no network restrictions. Medicare Advantage can be cheaper but has trade-offs. Choose during your Medigap open enrollment window — switching later is harder.
• Stop HSA contributions when you enroll in Medicare Once you enroll in Medicare Part A or B, you cannot make new HSA contributions. Stop contributing the month before your coverage begins. Existing HSA funds can still be used tax-free forever.
• Review prior 2 years' income for IRMAA impact Your Part B premium at 65 is based on your income from 2 years prior. If you had a high-income year (large Roth conversion, asset sale), you may owe IRMAA surcharges. Know this before your first Medicare bill arrives.

The Bottom Line

Healthcare in early retirement is manageable — but it doesn't manage itself. The retirees who get it right spend a few hours planning before they leave, not scrambling after. This checklist covers every phase from pre-retirement prep to Medicare enrollment. Work through it in order and you'll arrive at each milestone ready.

The most expensive healthcare mistakes in early retirement are not medical bills — they're the structural ones: missed subsidy optimization, COBRA lapses, wrong plan selection, and delayed Medicare enrollment. This checklist protects you from all of them.