At first it was mildly uncomfortable for Stephen Bright, a supervisor with the city's parking office, to sit in front of a computer camera and speak to an out-of-state stranger who was challenging a ticket issued in Boston.
But as the conversation got underway, the online interaction wound up much like an ordinary in-person hearing.
"It is a little odd, because normally you're across from somebody, and you can hand documents back and forth," Bright said. "But it's very similar to the normal process. It's just kind of doing it a little bit differently."
The October hearing was the first in a new city initiative that will allow people who live outside of Massachusetts to log on remotely and contest their parking citations.
The effort — officials say they don't know of any other city with such a program — is intended to make the process easier to manage for those seeking due process from afar.
"It's about convenience, and being user-friendly as an office," Bright said.
To qualify for a Skype hearing, an individual must have a vehicle that's registered in another state. The person contesting the citation must also live somewhere other than Massachusetts.
Before a video conference can be scheduled, the alleged traffic offenders are asked to compile documents, such as photos, that are relevant to their cases and send them to the office of the parking clerk for review.
Typically, if someone is unable to attend a hearing because they live out-of-state, the driver can send someone to City Hall on his or her behalf. Tickets can also be appealed through e-mail or a letter.
City data show that people who appeal parking citations have a good chance of winning.
In fiscal 2015, 10,741 parking tickets were appealed at a hearing, and 8,107 — or about 75 percent — were dismissed. Officials could not say how many of those drivers were from outside of Massachusetts.
The city quietly announced the new program on its website in October. There have been five ticket appeals using Skype to date. In all cases, the tickets have been dismissed.
"That's not to say it is going to continue like that, because each case has its own individual circumstances," Bright said.
The first person to contest a ticket using Skype did so from his home office in New Hampshire, while wearing a T-shirt, on Oct. 26, according to Bright. That person won the case and thanked the city for its flexibility, he said.
"He actually complimented us in the end. He said he was impressed with the city's technological advancement, if you will, of how we do things," Bright said.
At least three more requests for Skype appeals are pending.
It takes two weeks, on average, from the time someone e-mails the city to request a hearing to the time the appeals process is completed.
"We are just trying to put the technology that's available and use the technology the best we can to give everyone an equal opportunity to have a hearing," said Stephen Maguire, director of the office of the parking clerk.
Bright is handling all of the inquiries for Skype calls until the department "works out the kinks" in the new program.
The city has no immediate plans to extend the service to Massachusetts residents. But officials aren't ruling it out.
"We can't say that we won't," said John DeStefano, adjudication manager and supervisor in the parking clerk's office. "But right now it's only with people traveling."
Correction: An earlier version of this story gave an incorrect percentage of parking tickets that are dismissed after they are appealed. The correct number is about 75 percent.