Medicare Annual Enrollment in Oregon: Deadlines and How to Switch Plans Before December 7

If you live in Oregon and have Medicare, the Annual Enrollment Period (AEP) is your yearly chance to change your coverage. It runs October 15 through December 7, so if you have not reviewed your plan yet, the clock is running.

This guide covers the Oregon deadlines that matter, exactly how to switch plans, and the mistakes to avoid.

The Oregon Medicare Deadlines to Know

AEP dates are set federally, so they are the same in Oregon as everywhere else. What changes locally is the set of plans and carriers available in your county.

• October 15: AEP opens. Your plan’s Annual Notice of Change (ANOC) should already be in your mailbox.
• December 7: Your request to join, switch or drop a Medicare Advantage or Part D plan must be received by this date.
• January 1, 2027: Your new coverage starts.
• January 1 – March 31: If you are in a Medicare Advantage plan, you get one chance to switch plans or return to Original Medicare. It is narrower than AEP, so do not treat it as a backup.

What You Can Change During AEP

During AEP you can generally:

• Switch from Original Medicare to a Medicare Advantage plan, or the reverse
• Move from one Medicare Advantage plan to another
• Join, switch or drop a Part D prescription drug plan

Medicare Supplement (Medigap) plans are different. They are not tied to AEP, and in many cases switching involves health questions, so read the Oregon note below before you drop any coverage.

How to Switch Plans: Step by Step

1. Read your Annual Notice of Change. Note changes to premiums, copays, drug tiers and provider networks.
2. List your doctors, clinics, hospitals and medications. Include dosages and your preferred pharmacy.
3. Check your county. Oregon plan options, networks and premiums vary by county, and a plan that serves Portland may not be offered in a rural area.
4. Compare total yearly cost, not just the monthly premium. Add copays, deductibles, drug costs and the plan’s out-of-pocket maximum.
5. Confirm every provider is in-network and every drug is on the formulary for 2027.
6. Enroll before December 7. Your new plan automatically replaces the old one, and you do not need to cancel separately.

If you do nothing, your current plan generally renews for 2027 with whatever changes it announced.

Oregon-Specific Cautions

Medicare rules are federal, but state rules shape some decisions.

• Dropping Advantage for a Supplement: Returning to Original Medicare is simple. Getting a Medigap policy afterward may require medical underwriting, which means you could be declined or charged more. Oregon has its own Medigap rules, so confirm what applies to you before you leave a plan.
• Network changes: Doctors and hospital systems can leave a plan’s network each year. Verify yours directly with the provider’s office.
• Free counseling: Oregon’s SHIBA program offers free, unbiased Medicare counseling. It is a good second opinion on any decision.

Who Should Compare Plans This Year

A review is worth your time if you:

• Take brand-name or specialty drugs
• Received a notice of a premium increase or benefit cut
• Had a change in health or in your doctors
• Are turning 65 soon and choosing coverage for the first time
• Have not compared options in two or more years

Get Help Before the Deadline

Legacy Wealth Services is an independent agency that works with a wide range of Medicare carriers, so you can see side-by-side options rather than one company’s pitch. We can check your doctors and prescriptions against available Oregon plans and walk you through enrollment.

• Read more on our Medicare page.
• Schedule a free plan review, or call 503-832-8555.

Starting early leaves time to compare, ask questions and enroll before December 7.

This article is for general information only and is not a substitute for personalized advice. Plan availability and benefits vary by location. We do not offer every plan available in your area. Please contact Medicare.gov, 1-800-MEDICARE, or a licensed agent for details.