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Do I Have to Pass Medigap Underwriting When Leaving Medicare Advantage?

In most cases, yes. Unless you qualify for a guaranteed issue right or are still in your one-time Medigap open enrollment window, insurers can review your health history and can charge more or decline coverage. That is why the order of moves matters: get Medigap approval before you drop your Medicare Advantage plan.

Written by the licensed advisor team at Pinnacle Insurance Advisors · Last updated July 29, 2026

How Medigap Underwriting Actually Works

When you apply for a Medigap policy outside of a protected window, the insurance company is allowed to ask detailed health questions. Applications commonly ask about recent hospital stays, heart and lung conditions, diabetes complications, planned surgeries, and the prescriptions you take. The insurer can use your answers to accept you, charge you a higher rate, or turn you down.

This surprises a lot of people because Medicare Advantage works the opposite way. You can join or switch Advantage plans during enrollment periods with no health questions at all. Medigap only guarantees that same easy entry during your one-time Medigap open enrollment period, which begins when you are 65 or older and enrolled in Part B, and in a handful of protected situations after that.

The Exceptions People Miss: Trial Rights and Guaranteed Issue

Federal rules give you a Medigap trial right in two common situations. If you joined a Medicare Advantage plan when you were first eligible for Medicare and you are still in your first year on that plan, you can leave and buy a Medigap policy without underwriting. The same is true if you dropped a Medigap policy to try Medicare Advantage for the first time and you go back within your first year on the Advantage plan.

You may also have a guaranteed issue right when something happens to you rather than because of a choice you made. Examples include your Advantage plan leaving Medicare, the plan leaving your service area, or you moving out of the plan's coverage area. In these cases you can buy certain Medigap plans without health questions, but the window to act is short, so do not sit on the paperwork.

The Safe Order of Moves

Apply for the Medigap policy first and wait for a written approval before you drop your Medicare Advantage plan. If underwriting turns you down, you still have your current coverage and you have lost nothing. If you disenroll first and then get declined, you can be left with Original Medicare alone, which has no out-of-pocket cap on the 20 percent Part B coinsurance.

Timing matters too. Most people make this switch during the annual enrollment period, October 15 to December 7, with new coverage starting January 1. Medicare Advantage members also get a window from January 1 to March 31 to leave a plan. And remember that Medigap does not include drug coverage, so you will want a standalone Part D plan lined up for the same start date. Going without creditable drug coverage adds a late enrollment penalty of 1 percent for every month you wait.

A licensed advisor at Pinnacle Insurance Advisors can check your underwriting outlook for free before you touch your current plan. Call 1-877-826-0053.

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