2027 alertProvidence Medicare Advantage Plans, PacificSource, Regence BlueCross BlueShield of Oregon and 5 other companies end some Medicare Advantage plans in Oregon on December 31. (CMS data) 24 days left in Annual Enrollment (ends Dec. 7).Is your plan ending? →
Retiree coverage

OEBB educator retirees and Medicare

OEBB (Oregon Educators Benefit Board) retiree medical coverage is for early retirees and ends when you become eligible for Medicare, on the last day of the month before your Medicare start date, unless you qualify for Medicare because of end-stage renal disease (OAR 111-050-0015). Dental may continue if your employer allows it. Most retirees then enroll in Medicare Parts A and B.

The Oregon Educators Benefit Board (OEBB), part of the Oregon Health Authority, provides health benefits for employees of participating Oregon education employers, such as school districts, education service districts and community colleges. OEBB retirees face the same basic turning point as PEBB retirees: OEBB retiree medical coverage stops when you become eligible for Medicare.

Who OEBB retiree coverage is for

OEBB's retiree guide defines an early retiree as an OEBB member who retires before 65, is not eligible for Medicare and receives a PERS service retirement allowance or another qualifying retirement benefit. Whether your former employer pays part of the premium is set by that employer's policy or bargaining agreement, so check with your district or college benefits office before you retire.

When OEBB coverage ends

Under OAR 111-050-0015:

  • Medical and vision end at Medicare eligibility. An early retiree who becomes eligible for Medicare can't continue OEBB medical or vision coverage. OEBB benefits end the last day of the month before the Medicare effective date.
  • ESRD exception. If you become eligible for Medicare because of end-stage renal disease, coverage can continue; OEBB's retiree guide says for 30 months.
  • Report Medicare promptly. The rule says to report Medicare eligibility within 31 days, or OEBB may take back coverage to the date you became eligible. OEBB's guide asks retirees to tell their employer as soon as possible.
  • Dental may continue if your employer's policy or bargaining agreement allows it.
  • Family members: dependents covered at retirement who aren't eligible for Medicare can keep coverage until they lose eligibility or become eligible for Medicare themselves.

Medicare enrollment at 65

Because OEBB medical coverage ends, plan to have Medicare Parts A and B start the first day of your Medicare month. Retiree coverage isn't coverage from current employment, so it doesn't give you a special enrollment period for Part B later. Sign up during your Initial Enrollment Period, the seven months around your 65th birthday month. A late Part B penalty adds 10% to your premium for each full 12 months you could have had Part B but didn't, for as long as you have Part B.

If you are still working for an OEBB employer at 65 with active-employee coverage, you can delay Part B without penalty until that job or coverage ends. See working past 65 in Oregon.

Your coverage options after OEBB

  • PERS Health Insurance Program (PHIP): if you retired under PERS, you can join PHIP's Medicare plans, which require Parts A and B and include prescription drug coverage. Tier One and Tier Two retirees with eight or more years of service may get the RHIA premium subsidy. See PEBB retirees and Medicare for PHIP enrollment windows and RHIA rules.
  • Individual Medicare coverage: Original Medicare with a Medigap policy and a Part D plan, or a Medicare Advantage plan. Your first six months with Part B at 65 are your Medigap open enrollment period. See Medigap in Oregon.
  • A spouse's employer plan from current work, if available.

Part B premiums

You pay the Part B premium to Medicare ($202.90 a month standard in 2026), usually from your Social Security benefit. OEBB doesn't pay it. If your income two years earlier was above $109,000 (single) or $218,000 (married filing jointly), you also pay IRMAA. For 2026, that means your 2024 income.

Part D and drug coverage

OEBB pharmacy coverage ends with your medical coverage. You then need Medicare drug coverage: a PHIP Medicare plan (all include drug coverage), a standalone Part D plan with Original Medicare, or a Medicare Advantage plan with drug coverage. Enroll so there's no gap of 63 days or more after your OEBB coverage ends, or you could owe a Part D late-enrollment penalty. Keep the creditable coverage notices OEBB sends. In 2026 Part D caps your out-of-pocket drug costs at $2,100.

If you retire at 65 or later

If you work past 65 with OEBB active-employee coverage and then retire:

  • You have a Part B special enrollment period for 8 months after your job or that coverage ends, whichever comes first. Don't wait for the end of it: sign up so Part B starts when OEBB coverage ends.
  • You have 63 days after losing creditable drug coverage to join a Part D plan without a penalty.
  • When you first enroll in Part B, your six-month Medigap open enrollment period starts.
  • For PHIP, check the 90-day enrollment windows with PERS Health (1-800-768-7377).

Resources and contacts

  • OEBB: OEBB Retiree Guide
  • Your district's or college's benefits office: retiree eligibility and employer contributions
  • PERS Health Insurance Program: 1-800-768-7377; pershealth.com
  • Social Security: 1-800-772-1213 (TTY 1-800-325-0778), for Medicare enrollment
  • 1-800-MEDICARE (1-800-633-4227, TTY 1-877-486-2048) and Medicare.gov
  • Licensed insurance agents: to compare individual Medicare plans from the companies they work with, you can request a call from a licensed insurance agent.

PEBB retirees and Medicare

PHIP and the RHIA subsidy.

Working past 65 in Oregon

Timing Medicare with employer coverage.

Medicare Part D in Oregon

Drug coverage and creditable coverage rules.

Sources

Frequently asked questions

Are OEBB retiree benefits the same as PEBB?

No. OEBB and PEBB are separate boards within the Oregon Health Authority. OEBB covers employees of participating education employers such as school districts and community colleges; PEBB covers state agency and university employees. Both end retiree medical coverage when you become eligible for Medicare.

Do all Oregon educators get OEBB retiree benefits?

No. OEBB defines an early retiree as a member who retires before 65, is not eligible for Medicare and receives a PERS service retirement allowance or another qualifying retirement benefit. What your former employer pays toward retiree coverage depends on its own policy or bargaining agreement.

Can OEBB retirees skip Medicare Part B?

OEBB medical coverage ends when you become eligible for Medicare, so it can't replace Part B. Retiree coverage isn't coverage from current work, so if you delay Part B you can owe a lifelong late-enrollment penalty.

Can I keep OEBB dental after I get Medicare?

Possibly. OEBB rules let Medicare-eligible retirees keep dental coverage only if their employer's policy or bargaining agreement allows it. Medical, pharmacy and vision coverage can't continue.

Licensed insurance agents for Oregon

These independent insurance agents are licensed in Oregon and work with Benefits Life, the publisher of this site. When they enroll you in a plan, the agent and Benefits Life may be paid by the insurance company. Learn more.

Berenice Suarez

Berenice Suarez

Accepting new clients

Independent licensed insurance agent in Oregon

Colorado Springs, CO · English, Spanish

Chiara Lewis

Chiara Lewis

5.0 out of 5 stars (4 reviews on MedicareAgents.com)

Accepting new clients

Independent licensed insurance agent in Oregon

Littleton, CO · English

Colin Lewis

Colin Lewis

5.0 out of 5 stars (1 review on MedicareAgents.com)

Accepting new clients

Independent licensed insurance agent in Oregon

Littleton, CO · English

Mike Fortunato

Mike Fortunato

Accepting new clients

Independent licensed insurance agent in Oregon

Colorado Springs, CO · English

See all Oregon agents →

Request a call from

Only this agent gets your request. No cost to you.

Visit an insurance agency office in Oregon

These offices are independently owned by licensed insurance agents and agencies that work with Benefits Life, the publisher of this site. They are not Benefits Life offices. When they enroll you in a plan, the agency and Benefits Life may be paid by the insurance company. If you already have an agent, contact your agent for help with your plan. Learn more.

Advanced Benefits Insurance

7755 N Highway 101, Suite F13, Gleneden Beach, OR 97388

Hours: By appointment only — please call first.

Wheelchair accessible · Free parking · In-home visits available · Video appointments available

See all Oregon offices →