Medicare Open Enrollment doesn’t begin until October 15, but waiting until then to figure out what you need can turn a straightforward insurance review into a frustrating scavenger hunt. The Medicare Open Enrollment period runs from October 15 through December 7 each year, and changes selected during that window generally take effect January 1. Medicare’s own 2026 handbook tells beneficiaries to begin comparing their existing health and drug coverage with 2027 options starting October 1. If you’re preparing for Medicare Open Enrollment, however, there’s no reason you can’t organize the information you’ll need well before new plans become available for comparison. These seven items will make it much easier to determine whether your current coverage still fits or whether 2027 is the year to make a change.