Medicare’s annual open enrollment runs October 15 through December 7, 2026, and the decisions you make then take effect January 1, 2027. The six weeks before it opens are the best time to gather your documents, read the plan-change notice that arrives by September 30, and decide whether your current coverage still fits, so you are comparing plans rather than scrambling when the window opens.
🔍 When is my Medicare enrollment window?
Enter the month you turn (or turned) 65 to see your personal 7-month Initial Enrollment Period and how the Oct 15 – Dec 7 window applies to you.
Month and year of your 65th birthday:
General information, not enrollment advice; confirm at Medicare.gov or 1-800-MEDICARE.
Key Takeaways
Enrollment window: October 15 to December 7; changes start January 1, 2027
Watch the mail: your Annual Notice of Change (ANOC) must arrive by September 30 and lists every 2027 change to your plan
You can switch Medicare Advantage plans, move between Original Medicare and Advantage, or change Part D drug plans
Free, unbiased help is available through your State Health Insurance Assistance Program (SHIP)
Doing nothing keeps your current plan, including any premium, copay, or network changes it has made
What you can change during open enrollment
Change
Allowed Oct 15 – Dec 7?
Switch from one Medicare Advantage plan to another
Yes
Leave Medicare Advantage for Original Medicare (plus a Part D plan)
Yes
Join Medicare Advantage from Original Medicare
Yes
Change or drop a Part D prescription drug plan
Yes
Buy or switch a Medigap (supplement) policy
Not guaranteed; medical underwriting may apply outside protected windows
Medigap is the piece most people misunderstand. Open enrollment does not give you a guaranteed right to buy a supplement policy; that right generally exists only in the six months after you first enroll in Part B and in a handful of special situations. If your plan is to leave Medicare Advantage for Original Medicare with a Medigap policy, confirm in September that an insurer will accept you before you make the switch.
The six-week checklist
Week 1 (late August): gather your records
List every prescription with dosage and how often you fill it. This list drives the Part D comparison and is the single biggest source of savings.
List your doctors, hospitals, and pharmacies, including any specialist you expect to need next year.
Pull this year’s costs. Add up premiums, deductibles, copays, and drug costs from January through August to get a real baseline.
Create or log in to your Medicare.gov account. The Plan Finder can save your drug list and pharmacies so the comparison takes minutes instead of hours.
Week 2 (early September): understand your current plan’s 2027 changes
Watch for the ANOC. Every Medicare Advantage and Part D plan must mail it by September 30. It shows next year’s premium, deductible, copays, drug tier changes, and provider network changes side by side with this year’s.
Check the drug formulary specifically. A drug moving from tier 2 to tier 4, or being dropped entirely, can cost far more than a premium increase.
Confirm your doctors are still in network for 2027, not just 2026. Networks change every year.
Week 3 (mid-September): decide whether you need to shop
If your ANOC shows no meaningful changes, your doctors are still covered, your drugs are still on the formulary at the same tier, and your total cost this year was manageable, staying put is a legitimate choice. If any of those changed, or your health needs changed, plan to compare. People who compare Part D plans each year often find a cheaper option because drug pricing between plans shifts significantly from year to year.
Week 4 (late September): line up help
Book a SHIP appointment. State Health Insurance Assistance Programs offer free, one-on-one counseling from trained volunteers who do not sell insurance. Slots fill quickly in October, so booking in September matters.
Note the 2027 Part B premium and deductible when the government announces them, typically in the fall. They are deducted from Social Security checks and affect your net benefit.
Understand the Part D out-of-pocket cap. Since 2025 there has been an annual cap on what you pay for covered drugs, adjusted each year; the 2027 figure will appear in plan materials. Plans also offer a payment option that spreads costs across the year.
Week 5 (early October): preview plans
Plan details for the coming year are posted on Medicare.gov on October 1, two weeks before enrollment opens. Use that window to run the Plan Finder with your saved drug and pharmacy list, sort by estimated total annual cost rather than premium alone, and read the star ratings. A plan with a $0 premium and a restrictive network or high drug costs can be far more expensive than one with a modest premium.
Week 6 (mid-October): enroll
Once you have chosen, enroll online through Medicare.gov, by calling 1-800-MEDICARE, or directly with the plan. Enrolling in a new plan automatically disenrolls you from the old one, so do not cancel anything separately. Keep the confirmation number. If you change your mind, you can enroll again before December 7; the last enrollment received is the one that takes effect.
Common mistakes to avoid
Comparing on premium only. Total annual cost, including drugs and expected visits, is the number that matters.
Assuming your plan did not change. Even the same plan name can carry new copays and a smaller network in 2027.
Ignoring the mail. The ANOC is easy to mistake for marketing and discard.
Responding to sales calls. Medicare will not call you to sell a plan; unsolicited calls are a common source of enrollment errors and scams.
Missing the Medigap underwriting issue when leaving Medicare Advantage.
If you miss the window
Medicare Advantage members get a second chance from January 1 to March 31, when they can switch to another Advantage plan or return to Original Medicare with a Part D plan, but cannot move from Original Medicare into Advantage. Special enrollment periods also exist for moves, loss of other coverage, and plan terminations. Outside those, you are generally locked in until the next October.
FAQ
Does open enrollment apply if I have Original Medicare and no drug plan?
Yes. You can add a Part D plan during the window, though a late enrollment penalty may apply if you went without creditable drug coverage for more than 63 days after becoming eligible.
Is this the same as ACA marketplace open enrollment?
No. The ACA marketplace window opens November 1 and covers people under 65 without Medicare. The dates overlap, which causes confusion, but the programs are separate.
Can I keep my Medigap policy if I switch Part D plans?
Yes. Medigap and Part D are separate; changing a drug plan does not affect a supplement policy.
When will 2027 premiums be published?
Plan-level premiums appear on Medicare.gov on October 1. The standard Part B premium and deductible are announced by the federal government in the fall, usually before enrollment opens or shortly after.
A one-page summary to print
Late August: drug list, provider list, this year’s costs, Medicare.gov account. September: read the ANOC, check the formulary and network, book SHIP. October 1: preview 2027 plans and sort by total cost. October 15 to December 7: enroll and keep the confirmation. January 1: new coverage begins, so refill prescriptions and confirm appointments under the new plan in the first week.
Sources
Medicare.gov, Joining a health or drug plan and enrollment periods
Centers for Medicare & Medicaid Services, Annual Notice of Change requirements
State Health Insurance Assistance Program (shiphelp.org)
This is general information, not personalized insurance advice. Last updated August 26, 2026 · InfoBrief Staff
An HSA (Health Savings Account) is yours forever, rolls over every year, and requires a high-deductible health plan; an FSA (Flexible Spending Account) belongs to your employer’s plan, is mostly use-it-or-lose-it by year-end, and works with any health plan. Both let you pay medical costs with pre-tax dollars — but the HSA is also a stealth retirement account, which makes the choice bigger than it looks during open enrollment.
Side-by-side
HSA
FSA
Eligibility
Must be on a high-deductible health plan (HDHP)
Employer must offer it; any health plan
Rollover
Unlimited — yours for life
Use by year-end (small carryover or grace period if employer allows)
Portability
Keep it when you change jobs
Generally lost when you leave
Invest the balance?
Yes — grows tax-free
No
Tax treatment
Triple advantage: pre-tax in, tax-free growth, tax-free out for medical
Pre-tax in, tax-free out for eligible expenses
How to think about the choice
If you’re on an HDHP and healthy, maxing the HSA and investing it is one of the best tax deals in the U.S. code — after 65 it works like a traditional IRA for non-medical withdrawals. The FSA shines for predictable near-term costs (glasses, braces, a planned procedure): you get the full election amount available on day one of the year. The classic mistake is over-funding an FSA and racing to spend it on marginal purchases in December.
FAQ
Can I have both?
Only in the limited-purpose combo: an HSA plus a “limited-purpose FSA” restricted to dental and vision. A general-purpose FSA disqualifies HSA contributions.
What happens to unspent FSA money?
Unless your employer offers the grace period or a small carryover, it’s forfeited to the plan. Check your plan documents — this is set by the employer, not by you.
What each account actually pays for
Both cover the same core list of IRS-qualified medical expenses: doctor visits, prescriptions, dental work, glasses and contacts, therapy, and — since recent rule changes — many over-the-counter medicines and menstrual products without a prescription. Not covered by either: insurance premiums (with narrow exceptions), cosmetic procedures, and general wellness items like vitamins. When unsure, the pharmacy’s FSA/HSA-eligible label or your administrator’s app is the fastest check.
The HSA long game: receipts now, cash later
The most underused HSA strategy: pay today’s medical bills out of pocket, keep the receipts, and let the HSA balance stay invested. There’s no deadline on reimbursing yourself — you can submit a 2026 receipt in 2046 and withdraw that amount tax-free after decades of growth. Combined with the triple tax advantage, this turns the HSA into arguably the strongest retirement vehicle per dollar in the tax code. Requirements: an HSA provider with investment options (most sweep to investments above a cash threshold like $1,000–$2,000) and a folder of receipts.
Job changes and life events
Event
HSA
FSA
You quit or are laid off
Account and money go with you
Access generally ends (COBRA continuation possible); spend eligible claims before leaving
Mid-year plan switch off HDHP
Keep and spend the balance; just can’t contribute
N/A
New job offers both
HSA + limited-purpose FSA (dental/vision only) is the legal combo that maximizes both
Don’t confuse it with the Dependent Care FSA
A Dependent Care FSA is a separate account for childcare and eldercare costs (daycare, after-school programs, summer day camp) — different limits, different rules, and you can hold it alongside an HSA without conflict. During open enrollment the two FSAs appear side by side; electing the wrong one is a classic (and irreversible until next year) mistake.
Can my spouse and I both have accounts?
Two HSAs are fine but you share one family contribution limit. One spouse’s general-purpose FSA, however, disqualifies the other spouse’s HSA contributions — the most common household-level foot-gun; coordinate before enrolling.
What happens to my HSA at 65?
Withdrawals for any purpose become penalty-free (non-medical ones just count as ordinary income, like a traditional IRA), and the account can keep paying Medicare premiums and medical costs tax-free.
How much should you actually elect?
FSA rule of thumb: add up only predictable costs — known prescriptions, planned dental work, glasses — and elect that, not a hopeful round number. Forfeiture risk makes optimism expensive. HSA ordering: the common priority stack for savers is 401(k) up to the employer match → HSA to its max → back to the 401(k). The HSA jumps the queue because no other account offers deduction, growth, and withdrawal all tax-free.
When the HDHP (and thus the HSA) is the wrong choice
The HSA’s tax perks don’t automatically justify a high-deductible plan. If you have ongoing conditions with frequent visits, regular specialist care, or expected surgery, a traditional plan’s lower deductible can beat the HDHP-plus-HSA math even after taxes — run both plans against last year’s actual usage during enrollment. The HDHP shines for the healthy-and-saving; it punishes heavy utilization years.
Can I change my election mid-year?
Only with a qualifying life event — marriage, divorce, birth, adoption, or certain employment changes. Otherwise elections lock for the plan year, which is exactly why the enrollment-window math above matters.
Do FSA/HSA cards work everywhere?
They’re restricted to merchants and items coded as medical. At mixed retailers the register auto-splits eligible items; for anything else you pay normally and submit a claim with the receipt.
Last updated: August 22, 2026 · InfoBrief editorial team. Contribution limits adjust annually — check IRS figures for the current year during enrollment.
Quick answer: The deductible is what you pay before the plan starts sharing costs. A copay is a flat fee per visit. Coinsurance is your percentage after the deductible. The out-of-pocket maximum is the ceiling on what you can lose in a year, and it is the single most important number on the page. Premiums are what you pay to have the plan at all, and they do not count toward any of those limits.
Key Takeaways
Premiums never count toward your deductible or out-of-pocket maximum
The out-of-pocket maximum is your worst-case ceiling and the most important number to compare
Compare total annual exposure: 12 months of premium plus the out-of-pocket maximum
All these limits apply to in-network care; out-of-network often has separate and higher limits
The No Surprises Act protects you in emergencies and for out-of-network providers at in-network facilities
Health Plan Comparison Tool
Enter two plans and an estimate of your yearly medical costs. This shows what each plan actually costs you in a light year, a heavy year, and the worst case.
Plan A
Plan B
This is an estimate for in-network care. It assumes costs apply to the deductible, then coinsurance, capped at the out-of-pocket maximum. Copays, services covered before the deductible, and separate prescription tiers are not modeled. Check the Summary of Benefits and Coverage for each plan.
The four numbers, in the order money actually moves
Plan documents list these terms alphabetically, which is why they confuse people. Here is the order you actually encounter them.
Premium. A monthly charge for having coverage. You pay it whether or not you see a doctor, and it does not count toward the deductible or the out-of-pocket maximum. It is the only one of these numbers you are guaranteed to pay in full.
Deductible. The amount you pay yourself before the plan begins paying its share. On a $2,000 deductible, the first $2,000 of covered care is yours. Important exception: most plans cover preventive care and some services at a copay before the deductible is met, so read what is exempt.
Copay. A fixed dollar amount for a specific service, such as $30 for a primary care visit. Predictable, and often applies from day one.
Coinsurance. After the deductible, you pay a percentage rather than a flat fee. A plan with 20% coinsurance means a $5,000 procedure costs you $1,000. This is where large bills come from.
Out-of-pocket maximum. Once your deductible, copays, and coinsurance add up to this number, the plan pays 100% of covered in-network care for the rest of the year. Premiums do not count toward it.
Why the out-of-pocket maximum matters more than the premium
Most people compare plans by premium because it is the number in the biggest font. That answers the wrong question. The premium tells you your cost in a healthy year. The out-of-pocket maximum tells you your cost in a bad one.
The real comparison is total annual exposure: twelve months of premium plus the out-of-pocket maximum. A plan with a $200 monthly premium and a $9,000 maximum exposes you to $11,400. A plan at $380 per month with a $4,000 maximum exposes you to $8,560. The second plan costs more every month and less when something goes wrong.
Which to choose depends on whether you could absorb the worst case. If a $9,000 bill would be catastrophic for your finances, the cheaper premium is not actually cheaper.
The distinction that causes the largest surprise bills
Every number above applies to in-network care. Out-of-network care often has a separate deductible, a separate and much higher out-of-pocket maximum, or no maximum at all.
The federal No Surprises Act protects you in situations where you had no realistic choice: emergency care, and out-of-network providers working at an in-network facility, such as an anesthesiologist or radiologist you never selected. In those cases you pay in-network rates.
It does not protect you when you choose an out-of-network provider knowingly. That is why verifying network status matters before a scheduled procedure, and why “my hospital is in network” is not the same as “everyone treating me at that hospital is in network.”
What to check before choosing, in fifteen minutes
Your doctors. Search each one in the plan’s provider directory, and call the office to confirm, since directories are frequently out of date.
Your prescriptions. Look up each drug in the plan’s formulary and note its tier. A drug moving from tier 2 to tier 4 can cost hundreds more per month.
Whether a referral is required. HMO plans generally require one to see a specialist; PPO plans generally do not.
The family deductible structure. Some plans require the entire family deductible to be met before anyone gets coverage; others let each member’s individual deductible apply.
What is exempt from the deductible. Plans that cover primary care and generics at a copay before the deductible behave very differently from plans that do not.
High-deductible plans and the HSA angle
A high-deductible health plan trades a lower premium for a larger deductible, and qualifies you to contribute to a Health Savings Account. The HSA is the only account in the tax code that is untaxed going in, growing, and coming out for medical expenses.
The arithmetic that decides it: if the annual premium savings plus any employer HSA contribution exceeds the increase in your worst-case exposure, the high-deductible plan wins even in a bad year. If it does not, you are paying for a tax benefit you may not use. Our guide to how an HSA works and who qualifies covers the contribution rules and the Medicare timing trap.
FAQ
Does my premium count toward the deductible? No. Premiums are separate from every other number and never count toward the deductible or out-of-pocket maximum.
What resets each year? Deductibles and out-of-pocket maximums reset on the plan year, which is usually January 1 but may differ for employer plans.
Is a lower deductible always better? No. It usually comes with a higher premium. Compare total annual exposure rather than any single number.
What if I get a surprise bill anyway? Ask the provider for an itemized bill, compare it to your explanation of benefits, and dispute errors. If it involves emergency care or an out-of-network provider at an in-network facility, cite the No Surprises Act.
Where can I get free help comparing plans? HealthCare.gov has assisters and navigators at no cost, and employers usually offer a benefits counseling line during open enrollment.
Last updated: August 19, 2026. Written by the InfoBrief Editorial team. Rules and prices change; confirm with the official source before acting. See our disclosure.
