It comes as super PACs are taking a more prominent role in campaigning. Total spending on independent expenditures so far this cycle is nearly 2.5 times what it was at this point in 2020. And because candidates are having more and more trouble with small-dollar fundraising, super PAC money could be even more important as the cycle continues.

“As long as super PACs remain relatively under regulated in the way that they have been, the consultants who work for them and for various campaigns are going to continue trying to push the envelope using them in creative ways,” said Saurav Ghosh, director for federal campaign finance reform at the nonprofit Campaign Legal Center. “Because there seems to be very little risk in pushing against the supposed legal limits.”

The 2010 Citizens United decision opened the door for corporations, labor unions and other organizations to spend without limits as long as they don’t coordinate with campaigns. And advocates say the little enforcement since then has empowered groups to take advantage of loopholes.

Super PACs can raise unlimited money. That means a wealthy donor who can give only $6,600 to a federal candidate can give millions to an outside group backing them. Importantly, super PACs can also accept contributions from corporations and other entities that are barred from giving directly to candidates. They face few restrictions on spending, other than the coordination prohibition.

And outside spending continues to increase dramatically. Across all federal races, super PACs have spent more than $430 million on independent expenditures already this cycle, according to FEC data, up from $176 million at this point in 2020.

The expanded role for outside groups has been accompanied by new fundraising tactics and financial relationships.

A super PAC supporting Robert F. Kennedy Jr.’s independent presidential bid has repeatedly accepted million-dollar donations from a security consultant who is also the Kennedy campaign’s largest vendor, only to refund most of them months later. That has allowed the group to tout the contributions as part of its fundraising totals rather than loans it later pays back.

The super PAC, American Values 2024, describes the payments and refunds as “bridge funding.” The Democratic National Committee filed a campaign finance complaint about it, although that is not expected to be resolved until after the election. American Values 2024 also suggested it could spend to help get Kennedy on the ballot in some states, an unprecedented role for a super PAC. It later backed off that claim.

In other instances, Super PACs have begun to bridge the divide between a candidate’s outside ventures and their political pursuits.

Ahead of a competitive U.S. Senate race in Texas, iHeartMedia, which is home to a podcast hosted by Sen. Ted Cruz, gave hundreds of thousands of dollars to a super PAC backing Cruz, Truth and Courage PAC. An iHeartMedia spokesperson, Rachel Nelson, confirmed to POLITICO that the donations came from a portion of the podcast’s ad revenue. (Cruz himself isn’t paid for his work hosting the podcast.) The payments were first reported by the Houston Chronicle.

The GOP presidential primary also saw several examples of super PACs going further than they have before.

The super PAC backing Florida Gov. Ron DeSantis’ campaign received attention for first accepting more than $80 million from DeSantis’ former gubernatorial campaign — permitted because the Florida governor had ceded control of the committee before the money was transferred — and then by regularly hosting DeSantis as a “special guest” at events in GOP primary states. The super PAC also mounted a field operation in Iowa that was praised by DeSantis’ campaign, reflecting how it took on much of the traditional role of a presidential campaign.

The pro-DeSantis super PAC, Never Back Down, was the subject of several campaign finance complaints from outside groups, none of which have been resolved. While enforcement action against the group is unlikely, advocates also say the length of time it takes for the FEC to address complaints makes it easier for super PACs to act without concern.

Several super PACs backing GOP presidential candidates also sent fundraising texts and ran digital ads that enabled donors to give directly to campaigns, a practice not seen in previous presidential primaries.

The novel practices reflect an evolution for super PACs, building upon successful tactics in previous cycles, said Michael Beckel, a researcher at Issue One, a nonpartisan organization that advocates for reform on a range of issues, including money in politics.

“In the first couple post-Citizens United elections, you saw the B-roll,” said Beckel, referring to the practice where campaigns post video footage of candidates online, with super PACs then able to use it. “Now, the ways that candidates and outside groups telegraph messages to each other is much more nuanced and much more complex.”

Take “redboxing” — when campaigns leave public instructions for super PACs about the messaging that, they believe, would best support their campaign, often highlighted by a literal red box on a campaign website. Ethics watchdogs have long griped that the practice is essentially a form of coordination between super PACs and campaigns, but the FEC has sanctioned it on the basis that public statements do not amount to coordination.

More than 200 federal candidates used the practice in the midterms, according to a study published last month in the Election Law Journal. That’s a far greater number than previously documented, and demonstrates how common the practice has become. (Comprehensive data has not been available for earlier cycles.)

Redboxing continues to be popular.

In the upcoming Democratic primary in Pennsylvania’s 12th Congressional District, both Rep. Summer Lee (D-Pa.) and challenger Bhavini Patel, a councilmember from Edgewood Borough, have featured literal red boxes on their websites — and the suggested messages have since appeared in super PAC ads.

The box on Patel’s website included text accusing Lee of wanting “to ‘dismantle’ the Democratic Party.” On Tuesday, an ad launched by an anti-Lee super PAC, Moderate PAC, said Lee “even wants to dismantle the Democratic Party.”

Meanwhile, a red box on Lee’s website warned that attacks against her are funded by GOP billionaire Jeff Yass, who has been the biggest backer of Moderate PAC. A pro-Lee ad from Justice Democrats this week noted just that, saying attacks on her “are funded by a Republican billionaire.”

The continued boundary-pushing has frustrated ethics advocates, who have pushed for the FEC and other entities to up enforcement to little avail.

“We filed complaints against super PACs for presidential candidates. They were ignored. We took it to the Justice Department. They ignored it,” said Fred Wertheimer, a lawyer who has been working on campaign finance issues since the 1970s and is now president and CEO of Democracy 21, a nonprofit that has lobbied for stricter campaign finance reform. “And people know that.”