Medicare Open Enrollment Events for Senior Communities: A Host’s Guide

Hosting a Medicare open enrollment event at a senior or 55+ community is one of the most useful things a property team can do in the fall, as long as you set it up the right way. Medicare Open Enrollment runs from October 15 to December 7, and plan changes take effect January 1 (Medicare.gov). The safest format is an educational session led by an unbiased counselor from your state’s SHIP program, followed by private one-on-one appointments, with any insurance agents kept to a separate, clearly labeled event.

This guide covers who to invite, what federal marketing rules mean for your event, a planning checklist and the mistakes to avoid.

Why host a Medicare event at your community?

Every fall, residents receive plan notices, mailers and phone calls about coverage for the coming year. Many would rather ask questions in person, in a familiar room, without traveling. During Open Enrollment, people with Medicare can join, switch or drop a Medicare Advantage plan, add or change drug coverage, and move between Original Medicare and Medicare Advantage (Medicare.gov). Those are real decisions with real cost consequences, and a well-run on-site session makes the process less stressful.

It is not only a senior-community topic. Some residents under 65 qualify for Medicare because of a disability. In 2020, State Health Insurance Assistance Programs provided one-on-one counseling to more than 1.8 million people, including about 209,860 adults under 65 with disabilities (Administration for Community Living). Affordable and conventional communities can host the same kind of session.

Who should lead it: SHIP counselors vs. insurance agents

State Health Insurance Assistance Programs (SHIP)

SHIPs provide local, in-depth and unbiased counseling to people with Medicare, their families and caregivers, and there is no charge for the help (SHIP National Technical Assistance Center). In Texas, the SHIP is called the Health Information, Counseling, and Advocacy Program (HICAP) (SHIP locator for Texas).

SHIPs already do community outreach. According to ACL, SHIPs held 18,800 outreach events in 2020, including more than 4,000 enrollment events (ACL). Open Enrollment is a busy season for counselors, so contact your local program as early as you can.

Licensed agents and brokers

Agents can be knowledgeable and helpful, but they are paid to sell plans. If you invite one, treat it as a separate marketing event, tell residents exactly what it is, and avoid any appearance that the property recommends a particular company or plan.

What federal marketing rules mean for your event

Medicare Advantage plans and the agents who sell them follow federal communication and marketing rules. The key regulation for Medicare Advantage is 42 CFR 422.2264 (Cornell LII), and similar rules apply to Part D drug plans under 42 CFR Part 423. Your property is not the regulated party, but the rules shape what a plan representative can do in your clubhouse, so it helps to know the basics:

• Educational events must be advertised as educational. At an educational event, representatives may not market specific plans or benefits, give sales presentations, or hand out or accept enrollment applications. They may answer questions residents ask, hand out business cards and collect contact information or Scope of Appointment forms.
• Marketing events are different. Plan materials, presentations and applications are allowed. If a marketing event follows an educational one, attendees must be told the educational event is ending and be given a chance to leave.
• No sign-in requirement. At marketing events, representatives may not require a sign-in sheet or contact information as a condition of attending, and may not use health screenings to target attendees.
• Personal appointments need a Scope of Appointment. For in-person sales appointments, the products to be discussed must be agreed in writing beforehand.
• No unsolicited approaches in common areas. Plans may not approach people in common areas such as parking lots, hallways and lobbies.

This is general information, not legal advice. If you work with agents, ask them to confirm the event follows their carrier’s compliance requirements, and consult your own counsel with questions.

Medicare event planning checklist

Four to six weeks out

1. Pick the format. We recommend a 45-minute “What’s changing for next year” talk by a SHIP counselor, followed by 20- to 30-minute private appointments.
2. Book the counselor and confirm the details: date, length of session, how many one-on-one slots they can offer, and whether they need internet access or a projector.
3. Reserve two spaces: a main room for the talk and a private, quiet room or office for appointments. Personal health and income information should never be discussed across a crowded table.
4. Decide on agents. If you include them at all, schedule them on a different day and label the event “sales presentation by licensed agents.”

Two to three weeks out

1. Promote to every resident. Use flyers, email, your resident app and the front desk. Invite caregivers and family members who help residents with paperwork.
2. Write a clear flyer. Name the host (for example, “Free Medicare information session led by [local SHIP program name]”), note that the property does not sell or recommend insurance, and include a line on how to request accommodations such as large print or a sign language interpreter. Our accessible resident events checklist covers this in more detail.
3. Open appointment sign-ups at the leasing office or through your resident app, and keep the list private.
4. Share a “what to bring” list from the counselor. Counselors often ask for a Medicare card, current plan information and a list of medications and doses, but confirm with your counselor.

Event day

• Set up chairs with clear sight lines, a microphone if the room is large, and water.
• Post signs pointing to the main room and the private appointment room.
• Have a staff member greet residents, but keep staff out of one-on-one conversations.
• Offer a simple handout with the SHIP program’s contact information so residents can follow up after December 7.

After the event

• Count attendance and appointments (no health details) for your resident engagement report.
• Ask the counselor whether they can return for a “Medicare 101” session for residents turning 65 next year.
• Pair it with a fraud-prevention session. Our guide to scam awareness workshops for senior residents explains how.

Common mistakes

• Letting a sales event look like a property-endorsed event. Residents may assume your logo on a flyer means you vetted the plan.
• Collecting personal information at the door. Your team does not need Medicare numbers, medications or income details. Leave intake to the counselor.
• Scheduling too late. An event in the first week of December leaves no time for follow-up appointments before the deadline.
• Excluding residents. In a 55+ community, family members, caregivers and residents under the age threshold may still want to attend. Our fair housing resident events checklist explains why inclusive invitations matter.
• Treating it as a one-off. Medicare questions come up all year. Build it into your senior apartment activities calendar alongside health fairs and educational workshops.

Budget considerations

SHIP counseling is free to residents. Your costs are usually modest: printing, light refreshments, room setup, and staff time for promotion and check-in. If you already host an apartment health fair, a Medicare session can sit beside it as one of the “booths,” but keep the one-on-one appointments in a private room.

Frequently asked questions

When is the best time to host a Medicare open enrollment event?

Late October through mid-November gives residents time to book follow-up appointments before the December 7 deadline (Medicare.gov).

Can an insurance agent present at our community?

Yes, but it should be advertised honestly. If the event is billed as educational, the agent may not market specific plans or take applications under 42 CFR 422.2264. You may prefer to keep agents to a separate, clearly labeled event, or rely on SHIP counselors only.

Who are SHIP counselors, and do they cost anything?

SHIP counselors are part of state programs that give unbiased Medicare help at no charge (SHIP TA Center). In Texas, the program is HICAP.

Should property staff help residents choose a plan?

No. Staff can host, promote and set up the event, but plan selection should stay between the resident, their family and a qualified counselor.

How Roseway can help

Roseway Resident Services plans educational and wellness programming for senior, independent living and affordable communities in Dallas-Fort Worth, Austin, Houston and San Antonio, and at select locations nationwide. We can coordinate the room setup, resident promotion, accommodation requests, on-site check-in and follow-up reporting, so your team only has to open the doors.

If you want help adding a Medicare information session or a year-round education calendar to your community, contact Roseway to start the conversation.