Under increasing pressure over his performance, Oak Bluffs town administrator Michael Dutton is now the subject of a disciplinary proceeding in front of the town selectmen.

Selectmen have held two closed-door sessions within the last week to discuss Mr. Dutton’s performance under a section of the state open meeting law that allows executive sessions to discuss and consider the discipline or dismissal of a town employee. A third executive session is scheduled for July 5.

Mr. Dutton has not been named as the subject of the discussions, but the fact became apparent on Monday when selectmen reconvened in public session after meeting behind closed doors and announced that there were questions about Mr. Dutton’s contract and whether it had or had not been properly signed by him.

Declaring Mr. Dutton’s contract with the town “of no force and effect,” selectmen also announced that they had hired longtime labor attorney Jack Collins as special counsel. Mr. Collins is a partner with Collins & Weinberg in Shrewsbury.

A copy of the town administrator’s contract was requested by the Gazette yesterday, but selectman and board chairman Kathy Burton said she was unable to make the contract available to the public until receiving a determination from Mr. Collins.

Mr. Dutton has been the town administrator since 2006. His contract comes up for renewal every two years. Last year he was paid $117,000, according to the annual town report.

This year he has been at the center of a storm of questions swirling around the town’s fiscal problems, including violation of state bidding laws and an improperly posted special election.

In February the cash-strapped town was forced to call a special town meeting to make deep budget cuts after the Massachusetts Department of Revenue determined that town revenues failed to match up with projections. Another special town meeting was held this week when voters faced an additional $106,000 health insurance bill for town employees, which they agreed to cover from the town’s rainy day fund. Recently, Mr. Dutton also has acted as town finance director following the death of finance director Paul Manzi eight months ago.

In May a special election, called to address the town spending problems through two Proposition 2 1/2 override questions, turned out to be improperly posted. Mr. Dutton took responsibility for the error. Voters rejected both questions by a wide margin, and the state elections board said another election did not need to be called.

And this month the Massachusetts Attorney General’s office issued a strong reprimand to the town for violating the state bidding laws between 2009 to 2011. Among other things the attorney general report said the town gave the appearance of bid-splitting — an illegal practice of skirting public bidding laws by breaking payments into small amounts — when it made more than 100 payments totaling more than $180,000 to Powers Electric for electrical work on town projects. Mr. Dutton is the chief procurement officer for the town. He admitted that some electrical work had not been put out to bid properly, but vehemently denied the bid-splitting charge.

On Monday this week the five selectmen held their executive session in Mr. Dutton’s office; the session lasted for about 45 minutes. Mr. Dutton was not present, but town counsel Ronald H. Rappaport and town administrator assistant Alice Butler attended. Last Tuesday the board met behind closed doors for an hour and a half at the Oak Bluffs Library. Mr. Dutton was present at the meeting, along with Mrs. Butler.

Yesterday Ms. Burton said there were several different versions of Mr. Dutton’s contract circulating and that she was unclear whether one had been properly signed by Mr. Dutton. The version selectmen and counsel had been working with was from 2007, she said, and included the signatures of the selectmen but was missing those of Mr. Dutton and town counsel.

It is understood the issue of the signature on the contract is directly connected to how many votes would be required to fire Mr. Dutton. Without a signature, four votes are required; with a signature, three votes, or a simple majority, are required.

Ms. Burton said the motion to declare Mr. Dutton’s contract of no force and effect came at the recommendation of Mr. Collins, the special attorney, during a telephone conference during the executive session.

“The motion was labor counsel’s recommendation,” Ms. Burton said. “It was a technical motion because we were not able to find a signed contract by Michael.”

One selectman was uneasy with the motion.

“It’s a little unclear what that means,” said Greg Coogan during the brief public session on Monday. “I understand that it didn’t have a signature but I also understand that he’s been operating under it for a long time. If it’s recommended by [Ms. Burton] and labor counsel that we do that to move on with this I’m fine with it, but I have reservations.”

Mr. Dutton could not be reached for comment.

The July 5 executive session will be held at 4 p.m. in Mr. Dutton’s office in the town hall.