Free Medicare Help for Open Enrollment 2026: SHIP Checklist

Every fall, the mailbox fills up. Plan brochures, postcards with big phone numbers, maybe a call from someone who wants to “review your Medicare.” If you are 65 or older, or helping a parent who is, it can be hard to tell who is selling and who is simply helping.

There is one place built to be the second kind. Every state has a State Health Insurance Assistance Program (SHIP) — free, one-on-one Medicare counseling from people who, by federal law, are not supposed to have a stake in which plan you pick.

This guide is a checklist. It covers the 2026 dates, what to have on the table before you call, what a SHIP counselor can and cannot do, and the questions worth asking. It is based on Medicare’s own fall 2026 materials, the federal law that created SHIP, and the federal rules for plans and agents, as they read on September 14, 2026.

This is a government program. SHIPs are funded by federal grants to states under 42 U.S.C. 1395b-4 and run by state agencies with local partners. The rules below apply nationwide. Your state’s SHIP may use a different name.

Esta guía también está disponible en español.

The 2026 Dates, in One Table

Open Enrollment this fall is for your 2027 coverage.

Date	What happens	Source
By September 30, 2026	Medicare Advantage plans must tell members about changes that start January 1. The rule says “at least 15 days before” Open Enrollment begins — that works out to September 30 (our math).	42 CFR 422.111(d)(2)
October 1, 2026	Plans may start marketing 2027 plans. Medicare calls this the day to “get ready.”	42 CFR 422.2263(a); CMS flyer 11220
October 15, 2026	Open Enrollment begins.	Medicare.gov
December 7, 2026	Open Enrollment ends. The plan must get your enrollment request by this date.	Medicare.gov
January 1, 2027	New coverage starts. If you keep your plan, its new costs and benefits start too.	CMS flyer 11220
January 1 – March 31, 2027	If you are in a Medicare Advantage Plan, you can make one change.	42 CFR 422.62(a)(3)

You do not have to wait until October 15 to call. Comparing plans takes time with your drug list, and Medicare’s own flyer marks October 1 as the day to get ready.

What SHIP Is — and Why It Is Different From an Agent

A SHIP counselor and an insurance agent may both sit down with you and compare plans. The difference is who pays them and what the rules say.

	SHIP counselor	Licensed agent or broker
Cost to you	”There is no cost to consumers to use SHIP services” (SHIP center)	Ask the agent
How they are paid	Federal and state grants. “SHIP is not paid per enrollment” (SHIP flyer)	Plans can pay “compensation,” which the rule says includes “Commissions” and “Bonuses” (42 CFR 422.2274)
Conflict-of-interest rule	Staff, “including volunteer staff members,” must have “no conflict of interest” (42 U.S.C. 1395b-4)	Must be licensed and appointed under state law, and must document a “Scope of Appointment” before a sales meeting (42 CFR 422.2274)
What they help with	When to enroll, Open Enrollment changes, how Medicare works with supplemental (Medigap) policies, retiree coverage and Medicaid, and help paying costs (SHIP center)	Ask which insurance companies they represent

Medicare.gov puts it simply: “SHIPs aren’t connected to any insurance company or health plan” (Joining a plan). Agents are a legal option too — Medicare lists them — but it is worth knowing which kind of help you are getting.

Before You Call: The Checklist

A counselor can only compare plans with the details you bring. Here is what to have ready, and why.

Have ready	Why it matters
Your Medicare card	To join a plan you need “your Medicare Number and your Part A and/or Part B coverage start dates.” Medicare says: “Find this information on your Medicare card.” (Medicare.gov)
A list of every prescription you take — the name and strength on each label, and how often you take it	The key question is whether “the specific drugs you take” are on each plan’s drug list (CMS 11163). Medicare’s plan finder gives “customized coverage and cost information for your preferred pharmacies and any prescription drugs you take” (CMS 11220).
The pharmacies you use	”Check that your favorite pharmacy is in the network.” Some plans only cover drugs filled at their network pharmacies (CMS 11163).
Your doctors, specialists and hospital	Medicare’s advice: “Ask your doctors and pharmacies if they’re in the plan’s network” (Medicare.gov).
Your plan’s “Annual Notice of Change” letter	Medicare’s first step for this fall is to read it “to learn how costs and benefits may change in 2027” (CMS 11220).
Cards for any other coverage — job, union, retiree, Medigap, TRICARE or VA	”If you have employer or union coverage, call your benefits administrator before you make any changes” (CMS 11163). If you have Medigap, dropping it for a Medicare Advantage Plan can be hard to undo (CMS 11220).
A rough idea of your monthly income and savings, if money is tight	SHIPs help people apply for Medicare Savings Programs and Extra Help (SHIP FAQ). See our guides to Extra Help and Medicare Savings Programs for the 2026 limits.
The mail and call notes that confused you	Medicare warns you “might get a lot of mail from companies offering Medicare products” (CMS 11220). A counselor can tell you what a flyer is really offering.
Pen, paper, and your questions	Write down the counselor’s name and the plan names they mention.

If a family member is helping. Medicare needs your permission before it will talk to someone else about your case. You can give it with the “Medicare Authorization to Disclose Personal Health Information” form, or in your Medicare.gov account (CMS 12192).

How to Find Your SHIP

1. Go to shiphelp.org and pick your state or territory. There are 54 SHIPs — one in each state, plus Puerto Rico, Guam, D.C. and the U.S. Virgin Islands (SHIP center).
2. Or call the national SHIP center at 1-877-839-2675, or 1-800-MEDICARE (1-800-633-4227), TTY 1-877-486-2048. Medicare’s line is open 24 hours a day, including weekends (CMS 11220).
3. Look for a different name. Your SHIP “may go by a different name or acronym, such as HICAP, SHICK, SHINE, or VICAP.” A few of the biggest states, from the shiphelp.org locator:

State	Program name	Phone
California	Health Insurance Counseling and Advocacy Program (HICAP)	1-800-434-0222
Florida	Serving Health Insurance Needs of Elders (SHINE)	1-800-963-5337 (TTY 1-800-955-8770)
New York	Health Insurance Information, Counseling and Assistance (HIICAP)	1-800-701-0501
Texas	Health Information, Counseling, and Advocacy Program (HICAP)	1-800-252-9240

4. Ask how the appointment works. Depending on your area, counseling may be by phone, online or in person. Montana’s SHIP, for example, says a counselor “will meet with you in your home if you cannot get out or don’t have transportation” (Montana DPHHS). Rules like that vary by state, so ask.

Only call SHIP numbers from shiphelp.org, Medicare.gov, or your state’s own website. This guide does not link to any service that charges a fee.

What a SHIP Counselor Can Help With

• Comparing plans for 2027 — Medicare Advantage, stand-alone drug plans, and Original Medicare with Medigap. The law behind SHIP names Medigap comparison and long-term care insurance information specifically (42 U.S.C. 1395b-4).
• Enrolling in the plan you choose. Indiana’s SHIP, for example, says it “can help you compare and even enroll in plans that you choose” (Indiana SHIP).
• Help paying costs — applying for Extra Help and Medicare Savings Programs (SHIP FAQ).
• Billing problems, complaints and appeals. Medicare.gov lists “File a complaint or an appeal” among what SHIPs do (Talk to someone).

What SHIP does not do:

• Sign you up for Medicare Part A and Part B. That is Social Security: “The Social Security Administration (SSA) is the agency that handles Medicare enrollment for Parts A and B” (SHIP FAQ). SHIP can help you understand the timing.
• Sell or recommend a company. New Jersey’s SHIP says its counselors do not “sell, recommend, endorse any specific insurance product, agent, insurance company or plan” (NJ Human Services).
• Decide for you. “A SHIP counselor will not make decisions for you” (Montana DPHHS).
• Give legal advice (NJ Human Services).

Questions Worth Reading Off the Page

1. “Are all my drugs covered by this plan in 2027, and at what cost?”
2. “Is my pharmacy in the network? Is my doctor?”
3. “What is changing in my current plan on January 1?”
4. “Could I qualify for Extra Help or a Medicare Savings Program?”
5. “If I have Medigap now and switch to Medicare Advantage, could I get Medigap back later in my state?”
6. “If I change my mind after January 1, what are my options?”
7. “Do I need to cancel my old plan myself?” (Usually no — see below.)

Four Mistakes the Rules Can Save You From

1. Canceling your old drug plan yourself. When you switch during Open Enrollment, Medicare says “Your old drug coverage will end when your new drug coverage begins,” so “you don’t need to cancel your old plan” (Medicare.gov). Dropping coverage on your own can leave a gap. Going 63 or more days in a row without drug coverage that is as good as Medicare’s can mean a late penalty that generally lasts as long as you have Medicare drug coverage (CMS 11219).

2. Counting on January to fix a mistake. The January 1 – March 31 window is only for people already in a Medicare Advantage Plan, and you can make one change. CMS says you can’t use it to switch from Original Medicare to Medicare Advantage, or to switch from one drug plan to another if you’re in Original Medicare (CMS 11219).

3. Taking a surprise call as official. Under 42 CFR 422.2264, Medicare Advantage plans and their agents may not reach out without your request by door-to-door visits, social media direct messages, or “telephone solicitation (that is, cold calling), robocalls, text messages, or voicemail messages.” (Your own current plan is allowed to contact you about plan business.) If a stranger calls to “update your Medicare,” hang up and call your SHIP or 1-800-MEDICARE yourself.

4. Dropping Medigap without a plan to get it back. Medicare warns that if you drop Medigap to join a Medicare Advantage Plan, “You may not be able to get the same Medigap policy back later” (CMS 11220). There is one safety valve for new enrollees: if you join a Medicare Advantage Plan when you first turn 65, you can go back to Original Medicare within 12 months (42 CFR 422.62(c)). Ask a counselor about your state’s Medigap rules before you switch.

Where to Go Next

• Screen for every senior benefit at once. BenefitsCheckUp checks many programs in one sitting.
• Help at home, meals and rides. Your Area Agency on Aging handles the non-insurance side. SHIP services are delivered “in partnership with their local area agencies on aging and other community-based partners,” the SHIP center says.
• Drug costs still high? Compare prescription discount cards — and know how they work with Medicare.
• Need more care to stay at home? See whether PACE is offered where you live.

How We Checked This

What we opened and read ourselves, on September 14, 2026. The law that creates SHIP, 42 U.S.C. 1395b-4, from the 2024 U.S. Code on govinfo.gov. The federal rules for enrollment periods (42 CFR 422.62, 423.38), plan notices (422.111), marketing (422.2263), contact (422.2264) and agents (422.2274), which we pulled as the eCFR’s own XML for the title 42 issue of August 13, 2026. Medicare’s fall 2026 flyer “Your Yearly Medicare Review” (September 2026), its enrollment periods fact sheet (March 2026), its key dates and drug coverage fact sheets, and four Medicare.gov pages. The SHIP center’s About SHIPs, FAQ, flyer and state locator pages. State SHIP pages for New Jersey, Montana, California, Florida and Indiana.

Something you only see in the law itself. Most descriptions of SHIP say “unbiased.” The statute is more specific: to get the federal grant, a state must “provide assurances that staff members (including volunteer staff members) … have no conflict of interest in providing the counseling.” Many SHIP counselors are volunteers — and the law does not exempt them. The SHIP flyer adds the money side: SHIP is “not reimbursed by private health insurance plans” and “not paid per enrollment.” Compare the agent rule, 42 CFR 422.2274, where plan “compensation” for a sale expressly includes commissions and bonuses.

Where the common belief and the rules do not match.

• “You can only change plans in the fall.” Not for everyone. People with Medicaid or Extra Help can change drug coverage “once a calendar month,” Medicare’s March 2026 fact sheet says, and 42 CFR 423.38(c)(4) calls it a “one-time-per month election.” One oddity we found: a different rule in the same title, the marketing rule at 42 CFR 422.2263(b)(7)(i)(A), still describes these members as people who “may make changes once per calendar quarter during the first 9 months of the year.” That is the older limit. The enrollment rule and Medicare’s current fact sheet both say monthly, so that is what we tell you.
• “If I like my plan, I have to re-enroll.” No. Coverage “will continue automatically,” Medicare says. But the plan itself can change on January 1, which is why the notice deadline matters.
• “January 1 to March 31 is a second Open Enrollment.” It is narrower: Medicare Advantage members only, one change, and no switching into Medicare Advantage from Original Medicare.
• “SHIP is for people who are new to Medicare.” The SHIP flyer says plainly: “SHIP isn’t just for people new to Medicare.”
• “If they call me about Medicare, it must be Medicare.” Medicare Advantage plans and their agents are barred from cold calls, robocalls, texts and door-to-door visits you did not ask for.

What we could not check.

• ACL’s own SHIP page (acl.gov) returned HTTP 403 to every request, so nothing here rests on it. We do not give national counts of counselors or people served.
• Texas and New York state SHIP websites also returned HTTP 403. Their phone numbers above come from the shiphelp.org locator only. We confirmed the California and Florida numbers on the state sites too.
• Medicare’s plan finder and SHIP locator load with JavaScript we could not read, so we do not describe what a search shows. 2027 plan details are not in this guide.
• We did not book a SHIP appointment. We cannot tell you wait times in your area, or whether a Spanish-speaking counselor is available. Ask when you call.

Dates and rules above are federal and apply nationwide for Open Enrollment in fall 2026 (2027 coverage). SHIP names, phone numbers and appointment options vary by state. All sources were read on September 14, 2026.

Last updated: September 14, 2026

This is general information, not legal or financial advice.