Medicare Annual Enrollment Is Right Around the Corner. Medicare Annual Enrollment begins October 15 and runs through December 7 . This is the time for Medicare beneficiaries to review their current Medicare Advantage and prescription drug coverage for 2027. Plans can change from year to year, including premiums, prescription coverage, provider networks, copays, and other benefits. Don’t wait until the last minute. Crawford Benefits will be preparing for AEP throughout September—start gathering your updated medication, doctor, pharmacy, and coverage information.