Clinton Emails Raise Questions Over Secure Faxes And An 'Old Friend's' Influence A particular email drew scrutiny into whether Hillary Clinton had directed an aide to send secure material over an unsecure fax. And more emails from controversial adviser Sidney Blumenthal surface.

Clinton Emails Raise Questions Over Secure Faxes And An 'Old Friend's' Influence

Democratic presidential candidate Hillary Clinton speaks Tuesday during a campaign stop at the Osage Public Safety Center in Osage, Iowa. Charlie Neibergall/AP hide caption

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Charlie Neibergall/AP

Democratic presidential candidate Hillary Clinton speaks Tuesday during a campaign stop at the Osage Public Safety Center in Osage, Iowa.

Charlie Neibergall/AP

The latest batch of emails released from Hillary Clinton's time at the State Department contains more retroactively classified correspondence from her controversial private server.

The newly public 3,007 pages of emails include 66 documents with upgrades to "Confidential" status, according to a State Department official.

They were not classified at the time they were sent. The Democratic presidential candidate and her campaign have repeatedly stressed she never knowingly sent any classified information over her private server.

The new emails came at nearly 2 a.m. ET Friday, hours after the State Department had initially promised the latest release. The new documents were an effort to comply with a court order to release 82 percent of Clinton's correspondence by the end of 2015 — a goal the agency fell short of last week. But the new material brings it to that goal, and 43,148 pages have now been released since May.

One particular email drew scrutiny Friday — a June 17, 2011, exchange between Clinton and adviser Jake Sullivan. In that email string, she tells Sullivan she did not receive the evening's talking points — typically specifics used to speak to the press and for briefings.

"They say they've had issues sending secure fax. They're working on it," he writes to Clinton. She responds, "If they can't, turn into nonpaper w no identifying heading and send nonsecure."

Much of the email, including its subject line, were redacted, making it difficult to discern the topic and full context of the document.

At Friday's briefing, State Department spokesman John Kirby declined to talk about Clinton's email practices specifically but said the State Department searched the system and "could find no evidence and no indication that the talking points, the documents in question in that email was emailed to Secretary Clinton."

He also pointed out that it is not uncommon for unclassified documents to be created, edited and shared on a classified system. In other words, just because something is on a classified system doesn't mean it was classified.

White House press secretary Josh Earnest was also asked about the document, but he said he wasn't familiar with the particulars and referred reporters to Clinton's campaign. An NPR request to the Clinton campaign for comment has not yet been returned.

Senate Judiciary Committee Chairman Chuck Grassley, R-Iowa, said in a statement that the specific email "raises a host of serious questions and underscores the importance of the various inquiries into the transmittal of classified information through her non-government email server."

Grassley asked, "How long has the State Department been aware of this email? Why is it just now being released? Was her instruction actually carried out? If so, has the FBI opened a criminal inquiry into these circumstances? President Obama's State and Justice Departments owe the American people swift and accurate answers to these questions. The former Secretary of State needs to finally come clean and be transparent about the email practices she used during her tenure at the department."

Clinton has defended her use of a private email server during her tenure at the State Department, but it has become a flashpoint in her presidential campaign and provided ammunition for her would-be GOP opponents.

In another email released Friday, Clinton ironically commented on a State Department employee's use of personal email for official business.

"I was surprised that he used personal email account if he is at State," she replied when Sullivan forwarded her the staffer's observations on Libya.

The emails also included several from Sidney Blumenthal, a longtime Clinton friend and confidant who has been the subject of scrutiny into how much advice he provided to Clinton at State while he was working for the Clinton Foundation.

Clinton told the Benghazi congressional committee last October that she "did not ask [Blumenthal] to send me the information that he sent me." But last year, when asked during a campaign event about her "old friends," she said she would continue talking to them.

The new batch of documents includes many from Blumenthal on myriad topics, including Libya, Egypt, Israel and the Muslim Brotherhood. He cites his own "sources with direct access" to top-level people.

Clinton often passes them along and thanks Blumenthal for several. "Best info yet," she wrote to Sullivan about one.

Some of her exchanges with Blumenthal are more lighthearted, in which she jokes that she can't believe she has become a "meme" after her infamous "texting" photo went viral and spurred "Texts from Hillary."

"Better than a candidate," Blumenthal writes in April 2012, and then gives her advice on how to handle the upcoming presidential election.

"Good not to campaign, good not to go to convention, good on revelations on Bin Laden raid, but should use speeches like VMI, Naval Academy to establish new pivot, new redefinition of U.S. strength in new era that also redefines the relative position of others," he tells her. "Should say there is a new 'metric' of international affairs (lots of people like that word, as much as 'meme'). You've done 'smart power.' ... By establishing this metric, setting the standards for international conduct and behavior, you make another point: that you have reestablished U.S. leadership."

Another email also shows Clinton sending a note to daughter Chelsea — using Chelsea's alias "Diane Reynolds" — on the night of the Sept. 11, 2012, Benghazi attacks in Libya that killed U.S. Ambassador Chris Stevens and three others.

"Two of our officers were killed in Benghazi by an Al Queda-like group: The Ambassador, whom I handpicked and a young communications officer on temporary duty w a wife and two young children. Very hard day and I fear more of the same tomorrow. Let's try again later," Clinton wrote.

Ally Mutnick and Michele Kelemen contributed to this report.