Nearly three years after it got off the ground, New Haven’s Democracy Fund is still trying to figure out its own rules.

Since the fund’s founding, each mayoral election has forced the board to define more closely and alter its rules as unanticipated circumstances arise and board members find themselves unsure of the organization’s jurisdiction. The bureaucratic haze has left candidates, activists and board members themselves adjusting and readjusting as they go.

Just last Monday, the board decided not to penalize Mayor John DeStefano Jr.’s 2007 reelection campaign for making a donation in 2008 to a New Haven political action committee and at the same meeting decided it needs to look into whether the mayor’s 2009 campaign may have inappropriate connections with another local political action committee. Democracy Fund Administrator Robert Wechsler said the “facts are complicated” and that he does not yet know whether the Democracy Fund has jurisdiction over the issue or whether it is a state matter.

The Democracy Fund is a government-run organization that provides public financing for municipal elections to candidates who qualify and agree to abide by the its rules, which cap individual donations and bar candidates from accepting funds from political action committees. DeStefano is the only political candidate to have received money from the Democracy Fund.

Finding itself in uncharted territory, the board has been left playing it by ear. For example, in deliberations last Monday about how much to fine the mayor’s 2009 campaign for filing its finance reports late, the board viewed the maximum penalty of $5,850 with 12 percent interest as unfair, and one member proposed a $1 fine instead. The board settled somewhere in between: $500, Democracy Fund board member and Yale Law School professor Dennis Curtis said.

The meeting at which the board decided not to fine DeStefano’s 2007 campaign for giving $12,500 to the James Hillhouse Society — a New Haven political action committee — occurred almost two months after the board learned of the possible infraction. It decided not to fine the campaign because the Fund’s rules at the time did not explicitly define the proper uses for surplus campaign funds, Wechsler said Sunday.

Now the Fund needs to decide whether DeStefano’s most recent campaign committed another violation when local political action committee Elm & Oak PAC paid DeStefano’s 2009 campaign manager, Keya Jayaram, and possibly paid for campaign expenses as well. The inquiry comes after the New Haven Register alleged in a recent article that the mayor’s 2009 campaign violated “the intent, if not the rules, of the Democracy Fund” because of the payments, Wechsler said.

Hector Rivera, the treasurer of the Elm & Oak PAC, said he does not know why the mayor’s relationship with Elm & Oak PAC is being scrutinized. He said that the Elm & Oak PAC did not pay for any of the mayor’s campaign expenses and that payments to Jayaram were only for work she did for the Elm & Oak PAC that was not a part of the mayor’s campaign.

Deputy Campaign Manager Ben Shaffer ’09 said there was nothing out of the ordinary in the relationship, including the fact that the political action committee and the mayor’s campaign shared an office.

In response to a question about the recent scrutiny of his campaigns, DeStefano said in an interview with the News on Friday that “people are welcome to scrutinize whatever they choose.”

Curtis said that while state law allows political campaigns to donate excess funds to political action committees, doing so skews the political playing field.

During the 2007 mayoral campaign, the Democracy Fund’s rules did not specify whether it would allow campaigns to donate excess funds to political action committees. But early this year, the Board of Aldermen amended the Democracy Fund’s rules to prohibit “participating mayoral committees” from making “any expenditures that are not qualified campaign expenditures,” Wechsler said. The amended rule was in effect for the 2009 mayoral campaign.

As a result, even though the board did not fault the mayor’s 2007 donation, Curtis said the Fund’s rules need to make clear that the Democracy Fund does not allow participating campaigns to donate to political action committees, even with surplus campaign funds.

To that end, Wechsler said Monday that he created a list of approved expenditures that campaigns can make with leftover funds, such as to a party committee or charity.

Curtis said the board should also specify how surplus funds can be used in the Democracy Fund contract that participating candidates are required to sign.

Adriana Arreola, the mayor’s former campaign manager and treasurer of the James Hillhouse Society, said she expected the board not to penalize the campaign for the 2007 donation.

“There was nothing in the ordinance to guide [the campaign] in 2007 so we followed state law and that’s why we gave the excess funds [to the James Hillhouse Society,]” she said.

Jayaram, the mayor’s 2009 campaign manager, did not respond to requests for comment by e-mail and phone.

The Democracy Fund Board’s next meeting Dec. 14 will address the relationship between DeStefano’s 2009 campaign and the Elm & Oak PAC, Wechsler said.