City demands $600,000 for advertising a rental
When the medical team finally gave 82-year-old retiree Sandra May clearance to leave the hospital, she should have been able to focus on her recovery. Instead, she returned home to the news that her local government had slapped her with nearly $600,000 in fines—over a simple website error.
Sandra May is a Hawaii homeowner who rents out a portion of her home to supplement her fixed income from Social Security. She’s lived in the same house since moving to Honolulu in 1968, first as a renter, and now as the owner.
Sandra May and her cat, at home in Honolulu. Photo Credit: Michelle Mishina Kunz.
That house has been a central character in her life’s story, seeing her through her career as a real estate agent, her son’s childhood, and her husband’s final years with Parkinson’s and dementia. It should be the place where she gets to peacefully live out her retirement, enjoying the beauty of Honolulu.
Instead, the City is demanding she drum up over half a million dollars to pay an unconstitutional fine—even though it would force her to sell and leave behind her home of nearly 50 years.
Sandra May with some family photos. Photo Credit: Michelle Mishina Kunz.
A ban on short-term rentals
The City of Honolulu closely regulates the local rental market. Its regulations include a blanket prohibition on renting out your property for less than 30 days—and, as of late 2019, even bans advertising short-term rentals. Anyone who violates that prohibition, even unknowingly, could be fined a staggering $10,000 a day.
Sandra found that out the hard way.
Sandra May working at her desk. Photo Credit: Michelle Mishina Kunz.
Over half a million dollars for a website error
After a serious car crash forced her into a lengthy hospital stay in 2024, Sandra returned home to find a letter announcing that the City was charging her $10,000 a day for each day that a website error had allowed inquiries about short-term rentals.
Sandra had set her account to allow only rentals that were 30 days or longer. But an unexplained error caused the system to allow users to check for short-term rentals as well, causing her to unknowingly violate Honolulu’s short-term rental ban for two months while she was in and out of the hospital
When Sandra got the letter, she immediately tried to correct the listing and contact the City to explain the website error and resolve the matter. After talking with the City’s employees, she believed she had done enough to close the violation. Life seemingly returned to normal.
Then, after a year of silence, the City decided it was time to collect.
Sandra May at home. Photo Credit: Michelle Mishina Kunz.
No way out but the courts
In 2025, the City sent her a new letter demanding the astronomical fines she thought had been dismissed in 2024. The same day, the City sent another letter stating that her rental listing was allowing inquiries about short-term rentals, so Sandra once again tried to resolve the website error and address the unpayable $600,000 fine.
Working to correct the rental listing brought no relief—nothing she or the website’s tech support team tried could correct the error. She was forced to take down the entire listing, rather than watch the City’s fines increase further. Now, she can’t even offer long-term rentals to bring in income to pay the fines she’s facing.
Trying to address the fines through the local government’s approved channels also failed. The City charged Sandra $400 each time she tried to appeal—for requests that went nowhere and only increased the cost of the fight she faced. Before long, she was priced out of appealing the fines.
The blows kept coming. The City quickly sent her a third letter putting a lien on her home and banning her from using any City services—even essential services like driver’s license renewal and vehicle registration. That ban made Sandra entirely reliant on other sources of transportation like expensive ride-sharing services and public transportation, which makes obtaining medical care an hours-long struggle.
Rather than give up hope, however, Sandra resolved to fight the City’s unjust action. She turned to the courts and to the Constitution for relief.
Sandra May enjoying her backyard. Photo Credit: Michelle Mishina Kunz.
Challenging the City’s shakedown
Sandra filed a lawsuit to challenge the City’s demand. Represented at no cost by Pacific Legal Foundation, she argues that Honolulu is using this short-term rental prohibition as a revenue-generating scheme that violates residents’ constitutional rights.
The U.S. Constitution prohibits the government from imposing “excessive” fines and fees. Sandra’s lawsuit argues that fining her $10,000 per day—all for a system error that accidentally allowed people to ask if a room would be available to rent for fewer than 30 days at a time—violates this protection. She’s asking the courts to shut down the City’s unconstitutional demand.
If her lawsuit succeeds, Sandra’s victory will allow her to keep the home she fell in love with in 1968, without having to hand the government hundreds of thousands of dollars for the privilege. It would also empower other homeowners to challenge similar abuses of power by their own local governments, strengthening protections across the country for ordinary people facing astronomical fines in violation of their constitutional rights.
