Reviewed by Russell Noga, Licensed Medicare Insurance Broker (all 50 states) — Last updated October 27, 2026
Key Takeaway
Yes, you can switch from a Medicare Supplement (Medigap) plan to Medicare Advantage, most often during Annual Enrollment, October 15 to December 7, 2026, for coverage starting January 1, 2027. Joining the new plan won’t cancel your Medigap policy, so you have to cancel it yourself, and getting Medigap back later isn’t guaranteed in most states.
2027 by the Numbers
$12.00
Avg. monthly Medicare Advantage premium for 2027 (CMS, Sept. 2026)
Dec. 7
Last day to switch for Jan. 1, 2027 coverage (Medicare.gov)
12 months
Trial right to return after your first Medicare Advantage plan (Medicare.gov)
4 states
CT, ME, MA and NY require yearly or year-round Medigap sales (KFF)
A low Medicare Advantage premium can look tempting next to a Medigap bill that climbs every year. Annual Enrollment for 2027 is open right now, so this is the window most people use to make the move.
The switch itself is simple. What trips people up is the order of the steps, a Medigap policy that keeps billing after the new plan starts and the question nobody asks until later: can I get my Medicare Supplement back if Medicare Advantage doesn’t work out? This guide answers all three.


