The 2008 election cycle has seen a dramatic expansion in the use of the Internet to engage people in the political process. But with the rapid growth of online political advocacy have come unforeseen issues about how to police campaign-related activities on the Web, forcing regulators to address questions never anticipated by campaign finance law.

The gaps in legal guidance on Internet campaigning have pushed two innovative political Web sites, ActBlue and VoterVoter.com, to seek advice on how campaign laws extend to their activities.

Both are using the Web to transform elements of campaigning, primarily by facilitating grass-roots involvement in fundraising and advertising. As a result, both have entered uncharted territory when it comes to the application of campaign finance restrictions.

In recent years the Federal Election Commission, which oversees the enforcement of federal campaign law, has begun to construct a regulatory framework focused primarily on the costs of Internet activity. Because campaign finance restrictions are premised on the distorting effects of money, the commission has held that the low cost incurred by many types of Internet activism — sending e-mail or posting video, for example — are exempt from regulation.

The FEC also has ruled that bloggers, like the traditional media, are exempt from finance regulations, and thus are free to endorse and communicate on behalf of political candidates and causes.

Those guidelines only mark a starting point, however, for regulating the many new ways political advocates are using the Internet.

For example, ActBlue, a Democratic political organization that doubles as a Web-based candidate clearinghouse, has created a fundraising apparatus for unnamed future candidates that raises questions not addressed in current campaign laws. These funds, which are given names such as “AZ-Sen Democratic Nominee Fund 2010,” have been around since the site’s inception in 2004. But only recently did Jonathan Zucker, the organization’s executive director, raise a key question: which election cycle do donations to these funds apply to?

According to Marissa Doran, ActBlue’s director of strategy and communications, the absence of any legal guidance up to this point may have led to reporting inconsistencies, with some individuals reporting donations to future candidate funds during this year’s election cycle — while others who also contributed this year are waiting until the year the candidates actually run to report their donation to the FEC.

“My guess is that people have tracked these donations in all of the potential variations,” Doran said.

Given that there is a cap on the total contributions an individual can give in a two-year election period, deciding when to report such contributions is an issue for large donors. But it’s a question the FEC has never had to entertain until ActBlue came along.

A new company, VoterVoter.com., is raising issues that could have even deeper implications for campaign finance law. VoterVoter.com, which was formed in March, has taken a long-standing political practice — television advertising — and turned it on its head by giving users the tools to create and air their own political ads.

“We’re essentially providing an agency service that enables [individuals] to get their creative juices flowing and to put up an ad in whatever market they want at whatever budget they set,” said company executive Michael Rubiano.

The company charges standard licensing fees for ads it produces and commission fees for any airtime purchases made by individuals. It contends its activities fall within the exemption for commercial vendors who make and sell political communications in more traditional formats. VoterVoter.com also is requiring individuals that purchase airtime to report their spending with the FEC and include the proper disclaimers in the ads.

The biggest potential legal obstacle for the company could be how the FEC decides to define and regulate the involvement of political action committees that use its advertising services. VoterVoter.com, which allows different people to sponsor the same ad, is concerned the FEC could rule these individuals qualify as a political committee under the law.

“When you look at the way the law defines a PAC they premise it on the existence of a, quote, group. Before the Internet, it wasn’t hard to determine what that was,” said Joe Birkenstock, a counsel for VoterVoter.com and an election law attorney with the firm of Caplin and Drysdale.

“Only through the Internet, really, could you collect different individuals, each sitting in front of a computer, who literally will never have any meeting, real or virtual, other than ... they happen to pay for the same ad.”

VoterVoter.com also has asked the FEC whether individuals can pay to air ads posted on the site by PACs, if the ads do not identify the sponsoring committee in any way.

In theory, groups like MoveOn.org or Club for Growth could then post a Web ad of their own design on the site, which individuals could then pay to put on television.

But, as Birkenstock acknowledged, “When you start collaborating, the potential at least for limits comes in.”