Six questions to ask when switching to Medicare

The hand-off from employer health insurance to Medicare can be one of the trickiest challenges you will face in managing your retirement. The rules are full of pitfalls that can cost you thousands of dollars in unnecessary premiums or lead to a risky gap in coverage.

In this week’s Reuters column, I address some of the questions I hear most often from readers about the work-to-Medicare transition, including:

  • Is the Medicare enrollment process automatic?
  • Should I enroll in Medicare even if I am offered COBRA health insurance when I leave my job?
  • What if I am still working when I turn 65?
  • What if I want to execute a file-and-suspend strategy for Social Security? Could I contribute to an HSA in that situation?
  • Do I sign up for Medicare when I retire if my former employer provides a retiree health benefit?
  • What if I retire, enroll in Medicare and then go back into a full-time job?

Learn more at Reuters Money; also see my guide to navigating benefits if you’re working after age 65.

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