The post Medicare Backdated His Coverage Six Months. His HSA Contributions Became a Tax Problem. appeared first on 24/7 Wall St.. A 66-year-old software engineer decides to work one more year. He keeps his high-deductible health plan, keeps maxing out his HSA, including the catch-up contribution, and defers Social Security. When he finally retires in July and applies for Medicare, the enrollment specialist tells him something he did not expect: …