Once a year, and again whenever something big changes in your life. That’s the short answer. The longer answer depends on which kind of insurance you have, because each one has its own calendar.
Medicare: every fall
Medicare Advantage and Part D plans change their premiums, drug lists and networks every year. Your plan sends an Annual Notice of Change by the end of September, and the Annual Enrollment Period runs from October 15 to December 7. That is your window for an insurance review. If your prescriptions or doctors changed during the year, a plan that fit last January may not fit next January.
Individual health insurance: every open enrollment
If you buy your own coverage in Connecticut, open enrollment through Access Health CT is the time to compare. For 2027 coverage it runs from October 23, 2026 to January 15, 2027. Enroll by December 15 for coverage that starts January 1.
Employer plans: at each renewal
Group plans renew once a year, and the renewal is the natural time to look at whether the plan design and the cost still make sense. Business owners should also review when headcount changes. Crossing 20 employees, for example, changes whether federal COBRA applies and how the group plan coordinates with Medicare for employees over 65. Agents who handle small business health insurance can walk through what changes at each size.
Life events: right away
Some events shouldn’t wait for the annual review. Marriage or divorce. The birth or adoption of a child. Retirement. A job change. A move to another state. A new diagnosis or a new long-term prescription.
Several of these open a special enrollment window that closes after a set period. With Medicare, a move out of your plan’s service area gives you two full months to switch plans. Losing employer coverage gives you eight months to sign up for Part B. Miss the window and you may wait until the next enrollment period, sometimes with a penalty.
Life insurance: every few years, and after milestones
Life insurance doesn’t change yearly the way health plans do, but your needs do. Check the coverage amount and the named beneficiaries after a marriage, a divorce, a new child, a new mortgage, or the sale of a business.
What a review looks like
A review doesn’t have to end in a change. Bring your current plan documents, your list of doctors, your prescriptions, and anything that’s different from last year. Often the answer is that your current coverage still fits, and you can stop thinking about it for another twelve months.
If you’d like a second set of eyes when you update your insurance, call The Jones Group at (860) 529-3788.
