The latest batch of Hillary Clinton's private emails includes one that shows Clinton made an effort to help evacuate the acting Libyan prime minister from Benghazi amid a crumbling security situation.
It was released by the State Department just a week after congressional Republicans grilled Clinton for failing to respond to requests for more security from her own ambassador, who was killed in the 2012 terror attack in Benghazi.
The email shows Clinton received a request for supplies to help the acting prime minister leave Benghazi and transition into Tripoli, the nation's capital. Clinton seemingly greenlighted his request, and asked her aide Huma Abedin if the U.S. government could ship the requested supplies to a Libyan port.
The message from August 2011 is likely to give fresh fodder to her critics, who point out that requests for tighter security for U.S. officials never made it to her desk.
New emails released Friday also reveal the internal pressure Clinton faced while serving as secretary of State to coax the administration into launching airstrikes against Libya.
Sidney Blumenthal and Tony Blair, two close Clinton friends, fed Clinton information about Libya as the civil war there escalated, and encouraged her to take military action.
She was ultimately successful in rallying the U.S. government to do just what her friends were asking her to do, raising questions about how seriously she regarded the "unsolicited memos" Blumenthal sent her throughout her tenure.
Clinton publicly advocated for U.S. military engagement in Libya in 2011 on the basis of an imminent human rights threat. Blair, a former British prime minister and Clinton ally, urged Clinton to fight for a no-fly zone over Libya, something she successfully secured in 2011.
Blair seemed primarily concerned that the Libyan conflict was hurting the oil market. He was then serving as special envoy to the "Middle East Quartet," a diplomatic arrangement involving the U.S., the United Nations, the European Union and Russia.
"Please work on the no-fly zone, or the other options I mentioned," Blair wrote to Clinton in February 2011. "Oil prices are rising, markets are down. We have to be decisive."
Three days earlier, Blumenthal also urged Clinton to consider a no-fly zone, informing his friend in February 2011 that the British foreign secretary was pushing to implement one "like the no-fly zone imposed on Saddam's Iraq."
"US might consider advancing tomorrow," Blumenthal wrote to Clinton.
Clinton then forwarded the memo to Jake Sullivan, her directory of policy planning, for his input. "What do you think of this idea?" she asked.
Facing an unexpectedly robust challenge from Sen. Bernie Sanders, Clinton has been forced to move left on a variety of issues, including her support for the 2011 military intervention in Libya.
The former secretary of State argued strongly in favor of participating in airstrikes against the regime of Muammar Gadhafi, which ultimately helped depose the dictator but left Libya in chaos.
Pressed on her support of military action during a hearing before the House Select Committee on Benghazi last week, Clinton downplayed her personal advocacy for the airstrikes, framing the U.S. involvement as an administration-wide policy that she supported by association.
But her emails suggest Clinton was deeply involved in formulating the military position the administration eventually took in Libya.
Clinton's aides often forwarded her press clippings that praised the Libyan intervention and Clinton's role in securing it. In one instance, Clinton seemed unsure of her agency's record-keeping about her meetings with top Libyan officials.
"This is example of my continuing concern that we don't have our records ready," she wrote to an aide after a high-level meeting she attended was not noted in her records.
Other records showed Clinton with a seemingly casual approach to the conflict. For example, in response to a December 2011 email from Abedin about the attempted assassination of a Libyan rebel leader, Clinton replied, "Did you get info from Chelsea about the wall lamps?"
The batch of emails Friday was the largest published online to date. Many appeared to be duplicates of emails that were released previously, but the State Department claimed it was releasing roughly 7,000 pages of emails.
State Department officials had already released 19,569 pages of Clinton's private emails, many of them heavily redacted.
Hundreds of her emails have been classified at varying levels throughout the review process. Most of them have been marked "confidential," the lowest level of classification.
Clinton and her allies initially argued that none of the emails were classified, but shifted their phrasing to say none were classified "at the time" they were sent after the State Department began classifying portions of the emails.
The Democratic front-runner now tells inquisitors that none were "marked classified" when sent, a change that followed the inspector general's announcement that some emails "contained classified State Department information when originated."
The agency has repeatedly dismissed that finding, arguing the emails were only recently classified in light of circumstances that developed since the records were written.
While State Department officials maintain the designations are a routine part of the review process, critics have questioned how so many documents could suddenly become classified years after the fact.
The emails released so far have offered a limited glimpse into how Clinton conducted her State Department affairs.
Some records indicated Clinton's staff still harbored tensions from the 2008 primary in which Obama bested Clinton for the Democratic nomination.
Others revealed the former secretary of State's close ties to the Clinton Foundation while she was in office, a situation the White House had hoped to avoid by inking an agreement meant to prevent such activity.