Medicare's annual open enrollment runs from October 15 to December 7, 2026, and what you choose now shapes your 2027 coverage and costs. Instead of a generic checklist, we've sketched three hypothetical households. They're composites we made up to illustrate common situations, not real people. See which one sounds like you.
First, the changes that hit everyone
TheStreet's rundown of 2027 Medicare cost shifts highlights three things:
- A higher Part B premium. The projected standard monthly premium is $209.50 for 2027, up $6.60 from $202.90 this year. That's roughly 3.25%, or about $79 more per year for each person.
- A higher Part D out-of-pocket cap. The annual cap rises to $2,400 from $2,100, and the deductible ceiling rises to $700 from $615.
- The end of a federal premium-stabilization program for stand-alone Part D plans. That demonstration, which ran for 2025 and 2026, reduced premiums by an estimated $16 a month per enrollee this year, according to MedPAC. About 24.9 million people were in stand-alone Part D plans in 2026 (KFF). People who get Extra Help are shielded from the premium shift.

Projected Part B premium and Part D limits for 2027 compared with 2026.
One caution: the Part B number is a projection, and final plan-level premiums for 2027 haven't been released. Treat the figures as planning estimates.
Household one: Dana and Marcus, healthy and on Original Medicare
Imagine a couple in their late sixties. They've got Original Medicare plus a Medigap supplement and a stand-alone Part D plan. Neither takes many prescriptions. Their plan's Annual Notice of Change, which insurers must send by September 30, says the Part D premium is going up.
What they should do: Open the notice and compare the new premium and formulary with at least two or three alternatives on Medicare's Plan Finder. Because the stabilization subsidy is ending, premiums for stand-alone plans may move more than in the past, and a plan that was the cheapest this year may not be next year. If their drugs are cheap generics, the premium matters more than the deductible. They should also glance at their Medigap premium, since those can rise with age or inflation even though the benefits stay the same.
The trap to avoid: Staying put simply because switching feels like a hassle. It takes about 30 minutes, and plans change their pricing every year.
Household two: Ruth, on Medicare Advantage with a long-running health condition
Picture a woman in her seventies enrolled in a Medicare Advantage plan with a $0 premium. She sees several specialists and takes a handful of brand-name drugs.
What she should do: Look past the premium. In the Annual Notice of Change, check three things: whether her specialists and hospital are still in the plan's network, whether any of her drugs have moved tiers or require new prior authorization, and what the plan's maximum out-of-pocket limit is. Medicare Advantage plans can change networks, benefits and costs each year. If the plan no longer fits, she can switch during open enrollment, and if she stays in Medicare Advantage she also gets a second chance to change plans between January 1 and March 31, 2027.

Key dates for the 2027 Medicare enrollment season.
The trap to avoid: Assuming a $0 premium means $0 cost. The out-of-pocket maximum and the cost of specialist visits and drugs often matter more for someone who uses a lot of care.
Household three: Jim, still working at 66 with an employer plan
Picture a man who's turning 65 soon but works for a company with group health coverage. He's wondering whether to sign up for Part B and Part D now.
What he should do: Ask his employer's benefits office whether the group plan is considered "creditable" for drugs, and how it coordinates with Medicare. The answer depends partly on the size of the employer. Delaying Part B can be fine when you have qualifying employer coverage, but delaying without it can mean lifetime late-enrollment penalties. Part D works similarly: going without creditable drug coverage for 63 days or more can trigger a penalty that stays with you.
The trap to avoid: Relying on a coworker's story. Enrollment rules are specific to your employer, your work status and your birth date. Get the answer in writing from HR or from a licensed Medicare adviser.
Questions to ask before you switch anything
- Is each of my doctors, and my preferred hospital, in the network?
- Are all my prescriptions on the plan's formulary, and at what tier?
- What will I pay in a bad year, including the out-of-pocket maximum?
- Does the plan require referrals or prior authorizations?
- If I'm in Original Medicare and want to change Medigap, will I have to pass medical underwriting? In most states, switching Medigap after your initial enrollment window can involve underwriting.
Free help is available
Every state has a State Health Insurance Assistance Program, or SHIP, that offers free, unbiased counseling. You can also use Medicare.gov's Plan Finder, which lets you enter your drugs and pharmacy to estimate real costs. Beware of unsolicited calls or mailers that push you to switch quickly. Medicare will not call you out of the blue to ask for personal information.
A simple 15-minute routine
- Pull out last year's plan documents and this year's Annual Notice of Change.
- Write down your current premium, deductible and out-of-pocket limit.
- List your drugs, doctors and pharmacy.
- Run the Plan Finder with those details.
- If a better option appears, confirm the doctors and drugs by phone before you switch.
The bottom line
Medicare costs are creeping up in 2027, and the end of the Part D stabilization program makes this a year when shopping can really pay off. Whether you're healthy, managing a condition or still working, take the hour to compare. The window closes December 7.
Source
The households above are hypothetical illustrations. This article is general education and not insurance or medical advice. Medicare rules, premiums and deadlines change; confirm details with Medicare.gov, your state's SHIP or a licensed adviser.