Honolulu Widow, 83, Sues City Over $590K Fine from Website Glitch
An 83-year-old widow living on a fixed Social Security income in Honolulu is suing the City and County of Honolulu after a website error on a rental listing platform triggered $590,000 in fines — $10,000 per day for 59 days — threatening the home she has owned for 56 years. The case, filed May 28 in U.S. District Court, raises fundamental questions about the proportionality of municipal fines and the limits of government power under the Eighth Amendment.
The Story
Sandra May has lived in her home on Wilhelmina Rise in Honolulu since the 1970s. After her husband passed away in 2019, she relied on rental income from an attached one-bedroom unit to supplement her fixed income. That same year, the Honolulu City Council passed Bill 89, a strict ordinance aimed at curbing illegal short-term vacation rentals outside designated resort zones. The law made it illegal not only to operate an unpermitted short-term rental but also to advertise one, with fines of up to $10,000 per day.
May listed her unit on an online rental platform, setting the minimum stay to 30 days — a legal requirement under the ordinance. But according to the lawsuit, a glitch in the platform’s software allowed users to check availability for periods under 30 days, even though no short-term bookings could actually be made. May, whom her attorney describes as “technologically illiterate,” was unaware of the error.
A Hospitalization Turns a Mistake Into a Crisis
May received her first violation notice in November 2019 and corrected the listing, believing the matter resolved. A second notice arrived in 2023, and she corrected the listing again. But the third notice, issued in April 2024, arrived while May was hospitalized following a serious car crash and other medical procedures. Unable to check her mail for nearly two months, she returned home to discover that the fines had ballooned to $590,000.
According to Fox News, when May contacted city officials to explain the medical emergency and rectify the listing, their only response was to tell her to hire a lawyer. The city has since placed a lien on her property and blocked her from renewing her driver’s license and car registration.
“It feels to me like they’re just trying to take my house, put me on the street with the rest of the homeless people,” May told Fox News Digital. “It’s very depressing, very upsetting.”
The Legal Challenge
The Pacific Legal Foundation (PLF), a national nonprofit law firm that has won 18 of 20 cases before the U.S. Supreme Court, is representing May pro bono. The lawsuit, Sandra May v. City & County of Honolulu, Hawaii, et al., argues that the fines violate the Eighth Amendment’s prohibition on excessive fines.
“The Constitution prohibits excessive fines,” said Loren Seehase, the PLF attorney representing May, as reported by Hawaii Public Radio. “Governments cannot simply impose fines that are so ruinous that they would financially devastate someone over a simple error.”
Seehase emphasized that May never actually rented her unit for short-term stays. “This is not the type of situation where we’ve got like a building code violation and lives are imminently in danger,” she told Aloha State Daily. “This is an advertisement, so there was no harm done to anyone.”
Broader Implications
The case highlights a growing tension between municipal efforts to combat Hawaii’s severe housing crisis — where critics argue short-term rentals remove long-term housing from the market — and the rights of property owners facing potentially ruinous penalties for unintentional violations. According to Seehase, the city has issued more than $90 million in fines for similar advertising violations across Honolulu.
A 2025 investigation by the Honolulu Star-Advertiser found that the city has struggled to actually collect millions in fines from rental property owners, raising questions about whether the penalties serve as a deterrent or as a revenue-generating mechanism.
What’s Next
The federal court could partially or totally reduce the fines. May is not seeking monetary damages but rather relief from the penalties through the court. The case has strong parallels to Timbs v. Indiana (2019), where the U.S. Supreme Court ruled that the Eighth Amendment’s Excessive Fines Clause applies to state and local governments.
For May, the stakes are deeply personal. “All the stress, the stomach problems, every day wondering if I’m gonna have a house,” she told Fox News. “I was gonna live here for the rest of the days I have. This is actually — I call this my little piece of paradise on earth. The thought of losing it is — I can’t imagine.”
The city has declined to comment on the pending litigation.