Senior Obama administration officials knew since at least 2009 that Hillary Clinton was using a private email address to conduct official government business, according to a trove of some 3,000 pages of the former secretary of state's correspondence released by the State Department Tuesday night.

The emails show that White House chief of staff Rahm Emanuel asked for Clinton's email address on Sept. 5, 2009, three months after top Obama strategist David Axelrod asked the same question, the Associated Press reported.

What's not clear is whether officials knew that Clinton was exclusively using her private email account for official business, or that is was hosted from an insecure server based out of her home in Chappaqua, New York, which are against State Department guidelines.

Axelrod told MSNBC's "Morning Joe" in mid-June that he was unaware of Clinton's private server and "might have asked a few more questions" had he known she was using it exclusively.

As Vox notes, it's unlikely that any career-ending emails will be found in the newly released batch, as they have been meticulously picked through by State Department officials prior to release, and before State Department even had possession of the emails, Clinton controversially chose which emails she would allow to be archived in the public domain, and which she would delete. She eventually turned over 30,000 emails to State that she said were work-related. As for the remaining 30,000 some emails, Clinton decided they should be deleted due to their supposed personal nature.

Republican lawmakers maintain that such unilateral oversight gave Clinton the chance to whitewash any correspondence she didn't want to be publicly scrutinized, and they wonder if she was covering up Benghazi-related mishaps. In releasing previously undisclosed correspondence last week between Clinton and long-time adviser Sidney Blumenthal, House Benghazi committee lawmakers showed that Clinton had not actually turned over all work-related emails as she claimed, raising even more questions as to what she may be hiding.

While Clinton said she didn't send any classified material to anyone with her private email, the new release shows she did send or receive at least 12 messages in 2009 that were later classified as "confidential" by the government because they contained information relating to the intelligence community, or its production and dissemination of intelligence information, according to AP.

As Politico previously reported, at least one of her emails was later classified by the State Department, and at least 24 additional emails were marked "sensitive but unclassified." Being that Clinton sent highly sensitive information from a private server that security experts have warned was likely hacked multiple times, such revelations could raise legal implications.

In another email revealed on Tuesday, Clinton complained about President Obama not meeting with her frequently enough. Writing to her senior adviser Philip Reines, Clinton noted how former Secretary of State Henry Kissinger met with President Nixon "everyday," while she only meets with Obama "at least once a week."

"Do you see this as a problem?" Clinton asked.

Other emails show that Clinton struggled to fit into President Obama's White House after being appointed secretary of state in 2009. "I heard on the radio that there is a Cabinet mtg this am. Is there? Can I go? If not, who are we sending?" Clinton wrote.

One misunderstanding in 2009 showed Clinton showed up for the second time to a nonexistent meeting. "I arrived for the 10:15 mtg and was told there was no mtg," she wrote to aides. "This is the second time this has happened. What's up???"

Clinton inquired about a job for Blumenthal at the State Department in another email. Soon after, the Obama administration barred Blumenthal from coming on board due to a smear campaign he had waged against Obama during his presidential campaign.

Another email involving Blumenthal suggests that he and top Clinton aide Cheryl Mills worked together to place a hit piece in the media regarding Obama's national security adviser, James Jones. "Your request is being processed," wrote Blumenthal, including a link to a Huffington Post article that painted Jones as a "plodding, slow-moving, out of tough retired general."

Many emails were relatively mundane interactions, but nonetheless, they provide an interesting view into the life of a career politician.

In an email sent to staffer Huma Abedin on Oct. 19, 2009, Clinton asked about an event that was supposed to have taken place that fall in which she was supposed to be honored. "I thought there was an event this Fall (maybe even honoring me?). But, did it not happen or did I not go? What happened?" she asked. The email's subject line was "Allida Black's Eleanor Roosevelt human rights event."

Another showed that Clinton had difficulty working the fax machine in her office. Adebin instructed her to hang up the phone so people could call her.

"I thought it was supposed to be off the hook to work?" Clinton asked.

Perhaps the most mundane email was sent on Sept. 30, 2009, when Clinton sent an email asking for an aide to bring her some iced tea.

The State Department plans to continue to publicly release the 55,000 pages of Clinton emails, with the last batch expected to be unveiled on Jan. 29, 2016, three days before Democratic caucus-goers will vote in the Iowa caucus.