Medigap or Medicare Advantage? Decision Kit

Choosing between a Medigap (Medicare Supplement) policy and a Medicare Advantage plan? Most comparisons stop at premiums and extras. This kit starts with the question most people miss: if you change your mind later, can you come back?

Free copies available. Medical paperwork often lands when money is already stretched. That's not your fault. If paying isn't possible right now, email thedenialdesk@gmail.com with the subject "Free kit" and tell us which kit. You don't need to explain why. Please don't include medical details, diagnoses, bills or insurance numbers. Limit one free kit per email address.

Free updates: when a rule or date changes, your download link gets the updated file.

In most states, once your first Medigap window has passed, a Medigap company can ask about your health and turn you down. A KFF analysis published in October 2026, using 2023 data, found about 74% of people in Medicare Advantage have a health condition that could get a Medigap application turned down where insurers can use medical underwriting. That doesn't apply during your Medigap open enrollment period or when you have a guaranteed issue right. Knowing your rights before you choose matters.

WHAT YOU GET

• Decision guide (PDF, 14 pages). How the two paths work side by side, why Medigap can be a one-way door, the "can I come back?" checker (federal guaranteed issue rights and trial rights), a 50-state rules table, key dates, the 2027 numbers, questions to ask doctors and plans, and free help.
• 4 printable worksheets: my situation, my doctors and drugs, side-by-side costs, and SHIP call notes.
• Cost and dates calculator (Excel, opens in Google Sheets). Compares up to four options in a quiet year, an expected year and a worst-case year, and works out your Medigap and enrollment deadlines from your dates.

KEY DATES FOR 2027 COVERAGE

• Medicare Open Enrollment: October 15 to December 7, 2026
• Medicare Advantage Open Enrollment: January 1 to March 31, 2027

WHO IT IS FOR

People turning 65, people thinking about switching, people whose Medicare Advantage plan is ending, and family members helping them.

This kit is self-serve. It doesn't include personal help with your case. For free one-on-one help, see Who will help me for free?

The guide (PDF) reads fine on a phone. The calculator is easiest on a computer, or open it free in Google Sheets.

Still working and covered by a job plan? See the Still Working at 65? Medicare Timing Kit for when you can wait on Part B.

PLEASE NOTE

This is an educational planning tool. It is not insurance, legal, or financial advice, and it does not recommend any plan, company, or type of coverage. The Denial Desk does not sell insurance, is not an agent or broker, and is not affiliated with or endorsed by Medicare, CMS, any insurer, or any government agency. Rules vary by state; confirm with your state insurance department or a free SHIP counselor before you enroll or drop coverage. Instant digital download, nothing ships. For personal use only.

AI disclosure: This kit was drafted with help from AI tools, then reviewed and fact-checked by our founder, a certified medical coding professional.