Frequently Asked Questions
▸ Where can I find a free Medicare counselor like the one described who helped compare plan costs?
The State Health Insurance Assistance Program (SHIP) offers completely free, unbiased Medicare counseling in all 50 states — no sales pitch, no commissions. You can locate your nearest counselor at shiphelp.org or call 1-800-MEDICARE (1-800-633-4227). Most SHIP sessions are scheduled 45 to 60 minutes and can be done in person, by phone, or via video call depending on your state.
▸ What happens to my HSA if I switch from employer coverage to Medicare at 65?
This catches a lot of people off guard: the moment you enroll in Medicare Part A or Part B, you legally cannot make new contributions to a Health Savings Account. The IRS also applies a 6-month retroactive enrollment rule for Part A, which means you should stop HSA contributions at least 6 months before your Medicare start date to avoid a tax penalty. Your existing HSA balance can still be spent tax-free on qualifying medical expenses — including Medicare premiums.
▸ What is the Medicare Part B late enrollment penalty and how much could it actually cost me?
If you don’t have qualifying employer coverage and miss your Initial Enrollment Period around age 65, Medicare adds a 10% surcharge to your Part B premium for every full 12-month period you were eligible but unenrolled. In 2026, the standard Part B premium sits at $185.00 per month, so a two-year delay could permanently tack on $37 extra per month — every month, for the rest of your life on Medicare.
▸ Should I consider Medicare Advantage instead of Original Medicare Parts A, B, and D?
Medicare Advantage (Part C) plans bundle hospital, medical, and usually drug coverage, and many carry $0 monthly premiums in certain counties. As of 2026, about 54% of Medicare beneficiaries are enrolled in Advantage plans. The catch is narrower provider networks and prior authorization requirements for specialists. Out-of-pocket maximums on Advantage plans can reach $9,350 for in-network care annually, so it’s worth modeling your typical usage before assuming $0 premium equals lower cost.
▸ How long do I have to sign up for Medicare after leaving employer health coverage?
You get an 8-month Special Enrollment Period (SEP) starting the month after your employer coverage ends — or the month after your employment ends, whichever happens first. Missing that 8-month window forces you into the General Enrollment Period, which only runs January 1 through March 31 each year, with coverage not starting until July 1. That gap can easily mean 3 to 6 months without active coverage, so timing your employer exit carefully matters a lot.
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