The fall Medicare enrollment season brings a stack of mail, a run of TV ads, and a deadline. If it feels like too much, you’re not alone. Four steps cover what you need to do before December 7.
1. Know what’s changing this Medicare enrollment season
Medicare Advantage and Part D plans change every year, and 2027 is no exception. Premiums move, drug lists are revised, networks shift, and some plans are discontinued.
Your plan has to tell you. The Annual Notice of Change arrives by the end of September and lists every change to your costs, benefits and service area for the coming year. Read it before anything else. One number that applies to everyone with drug coverage: the Part D out-of-pocket cap rises to $2,400 in 2027, up from $2,100 in 2026, and the standard drug deductible rises from $615 to $700.
2. Get organized and compare early
The Annual Enrollment Period runs from October 15 to December 7. Don’t leave it to the last week.
Write down three things: your doctors, your medications with dosages, and the pharmacy you use. With that list, checking whether a plan works for you takes minutes. Then call The Jones Group to review your Medicare plan options.
3. Use sources you can trust
Enrollment season also brings phone calls and mailers that are hard to tell apart from official notices. A useful rule: plans and agents aren’t allowed to call you about Medicare plans unless you’ve given them permission. If someone calls out of the blue, you can hang up.
When you do talk to an agent, ask whether they are licensed in Connecticut and which insurance companies they represent. For free counseling with nothing to sell, Connecticut’s CHOICES program is at 1-800-994-9422. You can also talk with an independent agent at The Jones Group.
4. Take it one step at a time
Review, compare, confirm. That’s the whole process. If your current plan still covers your doctors and prescriptions at a cost you’re comfortable with, staying put is a perfectly good decision. If it doesn’t, you have until December 7 to switch, and the new coverage starts January 1.
If you have a Medicare Supplement plan
Fall enrollment is mostly about Medicare Advantage and Part D. Medicare Supplement (Medigap) plans work differently, especially in Connecticut. Every Medigap plan sold here is guaranteed issue year-round and community rated. You can apply to switch plans at any time without answering health questions, and your rate isn’t based on your age. If you have a Medigap plan, the part to review before December 7 is your stand-alone Part D drug plan.
If money is tight, check the Medicare Savings Program
Connecticut’s Medicare Savings Program helps pay the Part B premium, and at lower incomes it also covers deductibles and copays. Connecticut has no asset test, so savings and home equity don’t count; only income does. As of March 2026, a single person can qualify with monthly income up to $3,272. Qualifying also enrolls you in Extra Help, which lowers what you pay for prescriptions. You apply through the Connecticut Department of Social Services.
Missed December 7?
If you’re in a Medicare Advantage plan, you get one more chance after the Medicare enrollment season closes. The Medicare Advantage Open Enrollment Period runs from January 1 to March 31 and lets you make one change: switch to another Advantage plan, or go back to Original Medicare.
Whether you’re in your Initial Enrollment Period or thinking about switching plans this fall, The Jones Group can help. We work with individuals and families across Connecticut. Call (860) 529-3788.
