Union, district disagree on health insurance benefit cliff for those on strike in Portland

By Natalie Pate (OPB)
Nov. 17, 2023 2:23 a.m.

The district says Thursday was the cutoff for teachers needing to return to the classroom to be eligible for December benefits. But they expect teachers to still have coverage. Here’s why.

Portland Association of Teachers holding a rally outside of the Portland Public Schools district office in Portland, Nov. 7, 2023.

Portland Association of Teachers holding a rally outside of the Portland Public Schools district office in Portland, Nov. 7, 2023.

Kristyna Wentz-Graff / OPB

Members of the Portland Association of Teachers fear they’re about to lose their health insurance.


Thursday, Nov. 16, was the day Portland Public Schools officials said teachers needed to return to the classroom to be eligible for health care benefits this December. As the strike presses on, teachers remain on picket lines.

But the teachers’ union argues that, because of their work in October, they shouldn’t lose these benefits. They also say they were told before the strike began on Nov. 1 that they would be covered through December, and that it’s been a long-standing practice. They point to an email exchange with the district’s benefits director and confirmation from the state union’s lawyers as evidence that their coverage shouldn’t be ending.

However, the district also has confirmation from its human resources and legal staff that the union’s interpretation is wrong. They also say the district told the union as much before the strike began.

This is the latest example of a problematic back-and-forth between the two sides. District officials and union leaders haven’t agreed on several core bits of information about district operations and expenses over the past few weeks. The district’s ability to afford the union’s contract proposals is still being debated.

But health insurance can feel more personal than pay or job conditions. Health care affects not just the workers on strike but also their partners and children. Teachers and supporters have stressed that message in recent rallies.

On Thursday, demonstrators created a “healthcare wall” outside the district’s headquarters. They displayed dozens of photos, flowers and candles. PAT later shared a video of the display on Instagram, writing, “These are our family members who rely on our health insurance. Shame on PPS for playing these callous games.”

The union argues Portland Public Schools — regardless of the semantics on benefit coverage — has the power to make an exception due to the rare circumstances of the district’s first-ever teachers strike. Both sides have repeatedly said they didn’t want negotiations to reach the point of a strike, and now that it has, they both say they’re willing to do whatever it takes to get students and teachers back into schools.

But at the same time, the district worries about setting a costly precedent that allows employees in the future to not work for half a month and still claim benefits. This, while the district and union are already nickel-and-diming their way through contract mediations.

So, let’s sort through what each side is saying and try to understand the possible solutions.

What is the union saying?

Before the strike began on Nov. 1, PAT leaders released an FAQ to their members.

The information shared in the memo said that “because bargaining unit members earn their health insurance for the following month by working through the 15th of the current month, it would be unlawful for the district to withhold payment for health insurance that you have already earned just because you later participate in a strike.”

However, the FAQ continued, if the strike lasts for a long time, the district can “cease making additional monthly payments for your insurance for time you are not working.” PAT leaders said they would use the union’s hardship fund as needed should the district make that decision.

They then gave an example: A PAT unit member works from July 16th to August 15th and gets a paycheck on August 31st for that pay period. That August 31st paycheck will have insurance deducted to cover the employee’s September 1st – 31st insurance. If a strike began on September 1st, insurance would continue through the end of September.

This example was included in a September email exchange between PAT President Angela Bonilla and an official in PPS’ benefits department. Lawyers from the Oregon Education Association have confirmed PAT’s interpretation of the timeline for health insurance benefits.

Attorneys representing OEA filed an unfair labor practice complaint against the district Wednesday, saying PPS is unlawfully ceasing payments for PAT employee health benefits, therefore terminating their eligibility.

Noah Barish, one of the attorneys for OEA, also filed an affidavit to the state employment relations board, calling for an expedited decision on the complaint.

Since union teachers worked through October, the union maintains their members worked sufficient hours under PPS policy — the first half of a mid-month to mid-month pay period — and therefore, they should be covered through December.

What is the district saying?

If teachers aren’t working by Thursday, Nov. 16, they lose their eligibility for December health benefits. That’s how the district asserted the rule to OPB this week.

Now that the deadline is here, members must enroll in federal labor coverage, commonly known as COBRA.

PPS communications officials said this is because teachers must work half the month to qualify for benefits. While payroll considers a work period from mid-month to mid-month, they said that is not how benefit eligibility works.

The district confirmed teachers are covered through November because of their work in October, but eligibility is determined by each calendar month. Because they have not worked in November, they are not eligible for district benefits in December.

The district said that’s how it’s always been. The PPS website includes a standing benefits information page that provides such information.


District officials said this was posted “long before the strike and is the district’s long-standing practice.”

They also said they alerted the union about this before the strike began. They told members that if they strike, they will not be paid for strike days.

The district’s HR department sent a message to PAT members on Oct. 23 with an FAQ outlining this potential loss of benefits should the strike last a long time, as we’re seeing now.

The district later said they told PAT that the union’s information to members leading up to the strike — outlining a mid-month to mid-month eligibility period and, therefore, indicating they could be covered in December — was inaccurate.

Their notice to teachers in October said:

An employee who works or is paid for at least half of the scheduled contract days of the month, including paid holidays, will have coverage for the next calendar month. Coverage will terminate at the end of the month if an employee ceases to work or is not paid for half of the contract days of the month (except for summer months if the employee worked the whole school year).

If you do not work or are not paid for one-half of the contract days in November, it will impact your group health benefits for December. If you lose active coverage, you will be mailed a COBRA packet from the Trust Office and you could elect to continue coverage on a self-pay basis at the full cost of the plan. If you have any questions about COBRA, contact the Trust Office at 503-486-2107 or e-mail

This was later updated, communications officials said, to clarify that “if you have been on strike since November 1, 2023, and do not return to work by November 16, 2023, you will lose coverage after November 30 and have to elect COBRA for December coverage.”

The district’s communications department told OPB in an email Wednesday that the contrary messaging we’re hearing with the union now is “concerning,” so they “want to be crystal clear with PAT members.”

So, will teachers and their families lose coverage?

The short answer is no, but it depends. A few things could happen.

1. The two sides could reach an agreement. They have to at some point.

When this happens, the discrepancy may not matter.

District officials said a settlement agreement would likely wrap up loose ends, such as back pay, lapsed benefits, and other logistics for returning and recovering lost instructional time.

2. Other coverage and resources are available and will cover the costs.

The district is currently telling PAT members to apply for COBRA. Paperwork is supposed to be sent to their homes soon.

Renard Adams, chief of the district’s research, assessment and accountability department and a member of the PPS bargaining team, said the district doesn’t anticipate any teacher having a lapse in insurance because the OEA has committed to cover striking PAT members’ COBRA payments as necessary.

OEA president Reed Scott-Schwalbach previously told Willamette Week that OEA will ensure PAT’s members have health care coverage “until they have a fair contract.”

In other words, the district will stop paying, but teachers shouldn’t lose insurance because the statewide teachers’ union would pick up the tab — estimated to be about $5 million a month, as previously covered by OPB.

“For this, and so many other reasons,” Valerie Feder, director of media relations for PPS, said in a district statement, “we are eager for a resolution that reopens schools.”

3. The district might be able to make an exception and grant an extension.

It’s understood at this point that district leadership or the school board could theoretically decide to allow PAT members to still be covered in December, even while striking, given the rare circumstances.

This is what the union is calling for. They argue the district is making an active choice to cancel benefits for more than 3,500 employees. Some worry the process to get them all re-enrolled when this is over will be difficult and could result in some members slipping through the cracks.

However, it doesn’t seem likely that that will happen. District officials said earlier this week that PPS is worried about the precedent that would set — mainly that it could allow someone to not work for half a month in the future and still claim to be eligible.

What else is available for teachers in the meantime?

PAT has some hardship resources for folks participating in the teachers strike.

Participating members receive $120 a day from the OEA Relief Fund. Any sanctioned strike activities count for this, not just picketing.

PAT said members in good standing can also apply for a grant of up to $300 from OEA for unanticipated emergencies, such as utilities or medications. Members can also request reimbursement for interest on loans up to $500.

Many businesses across the city have also offered teachers free or discounted goods and services in recent weeks.