Angus McCoubrey started his vacation in Chilmark last week much as he has for the last 30 years visiting the Island, relaxing and going to the beach. An arrest based on a typo and a two-night stay in jail without possibility of bail or a hearing quickly turned that peaceful few days into a nightmare.

“It’s one of those things you don’t expect can happen to you. It’s amazing how the land of the free can turn you into a subhuman prisoner,” Mr. McCoubrey said. “No one had the correct information about anything.”

On August 21, Mr. McCoubrey and his wife Laura O’Connor decided to settle in for their annual vacation to the Vineyard, traveling from Philadelphia where Mr. McCoubrey, 37, is vice president and head of strategy at Red Tettemer O’Connell and partners, a creative agency. After about an hour of reading and relaxing at Lucy Vincent Beach, the couple decided to pack up and head home. While pulling out of the beach parking lot, Mr. McCoubrey got into a car accident that caused no injuries but smashed the rear passenger door of his car. Mr. McCoubrey said he called the Chilmark police to file a report for insurance purposes.

Shortly after driving away, Mr. McCoubrey realized his car was being followed by the officer who had responded to the accident. Mr. McCoubrey said he was pulled over at Beetlebung Corner and placed under arrest. When he asked why, the officer informed him that he was wanted for tax evasion in Brookline. Mr. McCoubrey was incredulous since he has never filed taxes in Brookline.

“I was like, ‘Is this a joke?’ And they said this is a very serious matter, this would not be a funny joke,” Mr. McCoubrey said of the arrest.

After being processed at the jail, Mr. McCoubrey said he discovered he would be held without bail. The warrant indicated he had missed a previous court date in the case, so he was denied bail by default because he was not to be trusted to show up this time around if released.The next morning Mr. McCoubrey learned he would be transported to Brookline to appear in court there on August 23.

Dukes County sheriff Robert Ogden confirmed Mr. McCoubrey was in custody from the night of August 21 until the morning of August 23 when sheriff’s deputies took him to Brookline. The sheriff’s department was following protocol by holding Mr. McCoubrey, Mr. Ogden said.

“We followed the orders of the court and transported him on that warrant up to Brookline,” Mr. Ogden said.

While in the Edgartown jail, Mr. McCoubrey said he hardly slept and suffered from panic attacks.

“Every minute that passes in a windowless cell with nothing to do feels like an hour at least,” Mr. McCoubrey said.

He said his treatment in jail was dehumanizing, though also left him with some memories of human decency. He noted that he’d been arrested in a wet bathing suit and flip-flops, but been told by a guard that his clothes would be laundered. The night before court, concerned he’d arrive in musty, wet clothes, he asked another guard he’d learned was sympathetic if they had been cleaned; they had not.

“He immediately got them washed for me,” Mr McCoubrey said. “I don’t know this guard’s name, but he treated me as a person, and I’ll remember his kindness to me for as long as I live.”

With nothing but time on his hands to think about the situation, Mr. McCoubrey said he realized what the mix-up was. In 2013, Mr. McCoubrey and a friend got into an argument with a taxi driver in Brookline over how much he owed in cab fare. After noticing the driver was taking them in the wrong direction, the pair asked to get out of the car. But the driver kept going for a few more blocks, which added extra money to the meter. The driver wanted $7 but Mr. McCoubrey and his friend were only willing to pay $5. The driver called the police, who issued Mr. McCoubrey a ticket.

“I was like, maybe there was a typo. It seems completely far-fetched that there would be that egregious of an error, but maybe,” Mr. McCoubrey said.

Mr. McCoubrey was right; he was in jail because of a typo. A copy of the 2013 criminal complaint provided to the Gazette shows Mr. McCoubrey was charged with tax evasion. But the original police report, also provided to the Gazette, says taxi fare evasion. The report also confirms the incident was due to a disagreement over $2. Shortly after that incident, Mr. McCoubrey moved to New York city, meaning he never saw the initial summons, he said.

“At that point I didn’t know that a civil ticket had turned into a felony warrant for my arrest,” Mr. McCoubrey said.

The case was dismissed in Brookline on August 23. Mark Wilson, a criminal defense attorney in Boston, confirmed he was hired to represent Mr. McCoubrey for the tax evasion charge. Taxi fare evasion carries a fine between $10 and $250. Tax evasion can result in up to two and a half years in prison and six-figure fines.

“There is a substantial difference between an allegation of tax evasion and a claim of taxi fare evasion; not the least being that the former is a serious felony,” Mr. Wilson wrote in an email to the Gazette. “While we don’t know how this happened, we appreciate the immediate dismissal from us pointing out what was clearly a clerical error.”

“I have no recourse for any kind of compensation; courts don’t apologize,” Mr. McCoubrey said .

On the afternoon of August 23, Mr. McCoubrey was on a boat back to the Island, a free but emotionally scarred man, he said.

“About half of my vacation was taken away and the other half is honestly just going to be spent reliving this,” Mr. McCoubrey said.

Editor's note: An earlier version of this story erroneously stated Mr. McCoubrey was told by an Edgartown bail commissioner that he was ineligible for bail.