Medicare & Healthcare

Health coverage in and around retirement — Medicare enrollment, IRMAA surcharges, HSAs, and long-term care.

5 articles in this topic.

Last updated: 2026-08-17.

• Coordinating Marketplace Coverage with Early Retirement

  Retiring before 65 makes the ACA marketplace your bridge to Medicare. The premium credit math, and why one mistimed Roth conversion can cost $20,000.

• Long-Term Care Planning Without Long-Term Care Insurance

  Traditional long-term care insurance is increasingly unobtainable. Self-funding, hybrid policies, the HSA stockpile, and the Medicaid rules that work.

• Transitioning from an HSA to Medicare

  Medicare enrollment ends HSA contributions. The six-month Part A retroactive trap, when to make your last contribution, and what to do with the balance.

• IRMAA Brackets and the Two-Year Lookback

  IRMAA adds as much as $487 a month to your 2026 Part B premium, based on income from two years earlier. The brackets, the cliff, and the appeal to file.

• Medicare Enrollment Basics: Parts A, B, C, and D

  The seven-month window around 65, the four parts of Medicare, the late penalties that never expire, and how it coordinates with employer coverage.