Government Turns Elderly Widow’s Tiny Website Error into Massive $600,000 Fine

This At Stake was published shortly before Sandra May successfully settled her case reducing the City of Honolulu’s initial fine by 95% and resolving all other claims against her. She then voluntarily dismissed her lawsuit, ending the legal proceedings.

At 83, Sandra May had already been through more than enough.

Her husband died following a long battle with dementia and Parkinson’s disease. COVID brought financial hardship. A serious car accident left her struggling to recover.

Then she opened her mail and discovered that a trivial website error—that she’d fixed already—had snowballed into a $600,000 city fine, pushing her toward foreclosure and financial ruin.

“I just wanted to bury my head,” she recalls.

Sandra arrived in Honolulu as a Navy wife in 1968 and never left. She built a successful real estate career, raised a son, and eventually purchased the home where she still lives today. For decades, her home’s small downstairs apartment provided extra, steady income as a long-term rental.

Then came the first series of setbacks: the death of her second husband in 2019, followed by COVID and two years of nonpaying tenants.

Now widowed, retired, and solely dependent on Social Security income, Sandra turned to online rental platforms to help find tenants.

“It was working wonderfully,” she said. “All the people that came just absolutely praised the place and said ‘thank God’ they found it, because they could never afford to come to Hawaii any other way.”

But Honolulu’s short-term rental laws created problems Sandra never saw coming.

The city prohibits rentals of fewer than 30 days and imposes steep penalties for violations—up to 410,000 per day. Twice, the city sent notices that dates on her online listing appeared available when they shouldn’t have been. Twice, she worked with the rental platform and fixed the problem.

“There again is another example of me thinking I’m doing right, but I’m doing wrong,” she says. “I called them up right away. I did what was necessary.”

Then everything got worse. In 2024, Sandra was seriously injured in a car accident. She spent the next eight weeks shuttling between hospitals, surgery, urgent care centers, emergency rooms, doctors’ offices, and rehab facilities.

Amid all this chaos, the city sent Sandra a third violation notice about her online listing, only this time, she never saw it—she lives alone and had no one checking her mail. She had no idea that even as she was recovering, Honolulu’s meter kept running: $10,000 a day, every day.

Sandra discovered the notice two months later and corrected the problem—only to learn that her fines had grown to a staggering $590,000—$10,000 for each of the 59 days it took to resolve the third violation. Due immediately.

“It was just one of those ‘You gotta be kidding me!’ moments,” she says.

Officials also placed a lien on her property and blocked her access to city services, including vehicle registration and renewal of her driver’s license. She knew fixing this new problem would require a lot more courage.

“It took some guts to make the phone call,” she says. “This was not my only problem, but it was the last straw.”

Fearful of triggering even more punishment, Sandra pulled her online rental ads altogether. Without renters, Social Security alone isn’t enough to cover rising expenses and Hawaii’s high living costs. And the property lien prevents her from selling or refinancing her home to come up with the funds.

“I’m just an old lady that lives in a house she can no longer afford,” she says. “I feel like I’ve never been able to retire. I have so much to do because of this and all the other little problems. There’s never a peaceful moment.”

Weaponizing a small mistake to collect more than a half-million dollars also raises a fundamental question for all property owners: Can the government impose ruinous penalties that bear little relationship to the alleged offense?

“The issue isn’t whether the government can enforce its laws,” explains PLF attorney Loren Seehase. “The issue is whether the government can use a minor violation to justify a punishment so extreme that it threatens an elderly widow’s home, livelihood, and financial future. The constitution says it cannot.”

Faced with fines she could never hope to pay, Sandra is fighting back. With free representation from Pacific Legal Foundation, Sandra filed a federal lawsuit to stop Honolulu’s unjust fines and protect the rights of all Americans from such excessive government punishment.

Looking back, Sandra has no regrets about taking on the city. In fact, she’s only doing exactly what city officials told her to do.

“When I called that last time, I said, ‘Let me get this straight: what you want is to put an 82-year-old woman out on the street, because that’s what you’re doing,’” she recounts. “I told them, ‘If you can insist on getting your $590,000, you’re taking my house away from me and there’s nothing I can do.’”

“That’s when they said, ‘Get a lawyer!’ So, boy, did I get a lawyer,” she adds. “I am all for the Constitution, so if we can prove them violating that, serves them right.”