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Residents of Bridgeport, Conn., are preparing to cast their ballots in what may be the most confusing election in the country.

A judge this week tossed out the results of the Democratic mayoral primary, citing surveillance video that appears to show significant voting irregularities. He ordered election officials to hold a new primary but had no authority to postpone the general election in the meantime. And so, on Tuesday, the general election will go on as planned.

What happens after that is uncertain.

“Obviously, we’re in very uncharted legal waters here,” said State Rep. Steven Stafstrom, a Democrat from Bridgeport and a co-chair of the legislature’s judiciary committee.

The city finds itself in this mess after videos surfaced that showed suspicious activity at absentee ballot drop boxes. In clip after clip, two women are seen stuffing wads of paper into the boxes.

“The videos are shocking to the court and should be shocking to all the parties,” Judge William Clark of the Superior Court in Bridgeport wrote in his ruling. He added, “The volume of ballots so mishandled is such that it calls the result of the primary election into serious doubt and leaves the court unable to determine the legitimate result.”

Although voting fraud is rare across the country, Bridgeport, a city of about 150,000 people in the southwest part of the state, has been dogged by election improprieties in recent years.

In June, the State Election Enforcement Commission, which is investigating the primary, said there was evidence of possible criminality in the 2019 mayoral primary. Last year, a judge ordered a new Democratic primary in a state representative race over allegations of absentee ballot fraud. In 2017, a judge ordered that a Democratic primary for City Council seats be rerun after a single absentee ballot, which was improperly handled, decided the race.

The incumbent mayor, Joe Ganim, was first elected in 1991 and served until 2003. He was convicted on federal corruption-related charges, resigned and spent seven years in prison. In 2015, he mounted a comeback and has been mayor ever since.

“We’ve been faced with a lot of disappointment, just over and over and over and over again,” said Joel Monge, 23, who runs Bridgeport Memes, a popular social media page.

The current legal fight started after the September primary in which Mr. Ganim beat his opponent, John Gomes, by 251 votes. Mr. Gomes challenged the outcome in court, citing the video clips, which were taken from municipal surveillance cameras stationed near the city’s four absentee ballot drop boxes. A clip appeared on social media days after the primary, leading Mr. Gomes’s lawyers to file a lawsuit to get all 2,100 hours of tape on the drop boxes.

Judge Clark ruled that just two women made or were directly involved in 15 incidents of drop boxes being stuffed with ballots. He wrote that the videos showed “credible evidence that the ballots were being ‘harvested’” — a process by which third-party individuals gather and submit completed absentee ballots in bulk, rather than individual voters submitting them for themselves, in violation of election laws.

Both women, the judge wrote, were “partisans” for Mr. Ganim.

Bill Bloss, Mr. Gomes’s lawyer, said his own review of the surveillance videos showed that no more than 420 people submitted ballots at Bridgeport drop boxes, but at least 1,253 ballots were submitted there.

Mr. Ganim denied any involvement. “I was as shocked as everyone when the video came out,” he said.

Both candidates said they were dismayed by the videos, and both men acknowledge that some of their supporters submitted multiple ballots.

“On both sides, there is video of the irregularities,” Mr. Ganim said. He added: “That’s not acceptable. We all want everyone’s vote to count. We all want fair elections.”

Mr. Gomes said his supporters had acted legally and had been submitting ballots for family members. The entire scandal is unfortunate, he said, adding, “Another black eye for Bridgeport.”

But the judge’s order focuses on Mr. Ganim’s supporters, some of whom appear to have submitted many ballots, many times.

“These instances do not appear to the court to be random,” Judge Clark wrote. “They appear to be conscious acts with partisan purpose.”

As a result of the primary confusion, choosing the city’s next mayor has become exceedingly complicated.

On Tuesday, the general election ballot will feature four candidates: Mr. Ganim; Mr. Gomes, now running as an Independent; David Herz, a Republican; and Lamond Daniels, an unaffiliated candidate.

If Mr. Gomes wins the general election, he intends to withdraw his complaint about the Democratic primary and, if necessary, formally ask the judge to cancel his order for a new vote. In that scenario, presumably, Mr. Gomes would just become mayor.

If Mr. Gomes does not win on Tuesday, but does win the second primary, he would advance to a second general election as the Democratic nominee. (Mr. Ganim would still be on the ballot, this time with the New Movement Party, according to Rowena White, his campaign spokeswoman.)

Alternatively, if Mr. Ganim wins the general election on Tuesday, and then wins the second primary, there would be no second general election, Mr. Bloss said. Mr. Ganim would be re-elected.

If one of the other two general election candidates wins on Tuesday, Bridgeport would hold a new Democratic primary and then a new general election.

Officials have yet to decide when a second primary would occur. Mr. Ganim or the city could still appeal the judge’s order calling for the new vote. And both campaigns would need time to get back into gear, even for a do-over vote.

For voters, the bizarre election spectacle has been dispiriting.

“There’s just not the checks and balances,” said Anthony L. Bennett, the lead pastor of Mount Aery Baptist Church, adding, “It’s a great city, with great people, that has had a troubling history with unchecked and unaccountable governmental leadership.”

Officials are trying to regain voters’ confidence. This week, Stephanie Thomas, the Connecticut secretary of state, appointed a temporary election monitor to oversee the mayoral election.

“The public should know that everything that can be done is being done,” Ms. Thomas said.

But critics noted that many absentee ballots have already been submitted for the general election — and questioned how one person could appropriately monitor the whole election.

And election skeptics across the country, who have long pushed to restrict voting by absentee ballot, have seized upon Judge Clark’s ruling.

They argue that Bridgeport — a historically Democratic city in a deeply Democratic state — is just one of the first places that absentee ballot fraud has been caught on camera.

“That this happened here is beyond reasonable doubt,” Elon Musk wrote on X, the site formerly known as Twitter. “The only question is how common it is.”

That worries many Democrats in Connecticut, including Mr. Ganim, who noted that many of his constituents struggle to access voting places on Election Day and need the option of absentee ballots. They may have health concerns, he said, or cannot get enough time off work to vote.

Many would-be voters in Bridgeport believe they have been let down by the government once again.

“A lot of people in Bridgeport just don’t vote in general just because they always assume Joe Ganim is going to win,” said Mr. Monge, who runs Bridgeport Memes.

But, he said, the videos had angered many of his friends, perhaps spurring them to participate: “I think a lot of people are going to go out and vote.”