The relationship between Hillary Clinton and the IT company that managed her personal email server is a lot cozier than previously reported, The Daily Caller has found.

Andy Boian, the CEO of dovetail solutions, which is handling PR for the Denver-based IT company, Platte River Networks (PRN), contributed $2,700 to Clinton’s campaign on July 8, 2015, Federal Election Commission records show.

News of the contribution, which was given a month before dovetail solutions was hired by PRN to handle the fallout from the revelation that it managed Clinton’s private email server, comes as Iowa Sen. Chuck Grassley, the chairman of the Senate Judiciary Committee, has raised questions over whether Clinton coordinated with PRN and others with intimate knowledge about her server by paying their PR and legal expenses.

Grassley’s concern is that by paying such expenses, Clinton is effectively controlling the companies’ responses to inquiries from government investigators and from the media. And Boian’s contribution suggests that he would be a willing partner to such an arrangement.

PRN executives have claimed that other than its work on Clinton’s server, the company has had no affiliation — political or otherwise — with the Democratic presidential candidate. The company has also claimed that it landed the contract for the server work by sheer luck.

In June 2013, PRN transported the server, which held emails containing classified information, from Clinton’s New York home to a data center in New Jersey. It remained there until August when the FBI seized the device.

Boian was brought on shortly after.

In a profile published in August, the Washington Post noted that none of PRN’s executives had donated to Clinton’s campaign. And though Boian had contributed to Clinton by that time, the donation was never disclosed.

In a letter sent last week, Grassley, a Republican, pointed to an invoice PRN allegedly submitted to Clinton’s accountant, Marcum, LLP, in September billing the company for legal and PR expenses.

Under two entries for “Legal activity re: Hillary Clinton,” PRN charged Marcum, LLP $2,720 and $25,733 for the periods July 24 and July 31 and Aug. 3 to Aug. 31, respectively. (RELATED: Senator Wonders If Hillary Is Covering Legal Expenses For Tech Firm That Managed Her Server)

PRN also appears to have billed Clinton to recoup what it paid Boian’s company.

In an entry dated Aug. 31, PRN charged $19,283 for “PR for Clinton email media inquiries.” Next to that entry is written, “dovet,” an apparent reference to dovetail solutions.

If Clinton’s accountant paid the invoice, the former secretary of state effectively would have paid PRN for its legal expenses and Boian for his PR work.

The Clinton campaign has avoided directly answering whether Clinton or any of her affiliates have paid PRN or any other company or former staffer. And Boian did not respond to TheDC’s request for comment on the invoice or on his campaign contribution.

For Grassley, the arrangement poses a potential conflict of interest.

“It is important for the Committee to know whether Secretary Clinton and her attorneys are providing financial support, legal support, or other coordination to those associates of hers who are involved in congressional committee and federal law enforcement inquiries relating to her email server,” Grassley wrote in a letter to attorneys for Clinton and several of her State Department aides, including Bryan Pagliano, her personal IT guy at the agency.

Pagliano worked as a staffer on Clinton’s 2008 presidential campaign before being hired by Clinton’s State Department in May 2009. There, Clinton reportedly paid him out-of-pocket to manage her server. Pagliano pled the Fifth Amendment in September during a brief interview with the House Select Committee on Benghazi.

Both the Senate Judiciary Committee and the Senate Homeland Security Committee, which is also investigating Clinton, have considered granting Pagliano immunity to testify about Clinton’s server arrangement.

In his letter, Grassley broached the possibility that Clinton is paying legal expenses for Pagliano and other former Clinton staffers. TheDC reported in September that Pagliano’s attorney, Mark MacDougall, works for Akin Gump, a Washington, D.C. law firm that has strong connections to Clinton.

For his part, Boian has recently showed signs that PRN will be less cooperative with investigators than it has been so far.

While Boian initially told various reporters that the company was cooperating fully with investigators, he recently said that PRN would not comply with investigators’ interview requests.

“We as a company have felt like we have done everything we can to comply with every request by both the FBI and the Homeland Security Committee, and we really have nothing left to give,” Boian told Politico. “We have a company to run.”

Ken Boehm, the chairman of the ethics watchdog group, National Legal and Policy Center, questions Boian’s contribution, especially in light of Grassley’s conflict-of-interest concerns.

“Everything about this routing of PR and legal expenses through the Clinton’s accounting firm makes this look like yet another Clinton damage control operation,” Boehm told TheDC.

“The fact that spin doctor Andy Boian of dovetail solutions just happens to be a current major donor to Hillary for America completes the picture.”

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