New emails released by a conservative watchdog group on Thursday appear to show former Secretary of State Hillary Clinton Hillary Diane Rodham ClintonWhat Senate Republicans have said about election-year Supreme Court vacancies Bipartisan praise pours in after Ginsburg's death Trump carries on with rally, unaware of Ginsburg's death MORE directing a top aide to call her via an unsecured phone line when technical troubles prevented a secure phone conversation.

“I give up. Call me on my home [number],” Clinton told then-chief of staff Cheryl Mills in a February 2009 email after more than an hour of trouble trying to communicate via a secure line.

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“I just spoke to ops and called you reg line — we have to wait until we see each other b/c [the] technology is not working,” Mills said in another email sent at almost exactly the same time.

“Pls try again,” responded Clinton, a few moments later.

It’s unclear whether the two did connect or if they moderated any discussion they may have had to avoid sensitive topics while on an unsecure landline.

But the episode is likely to cause concern among critics of Clinton, who have previously accused her of resorting to unsecure forms of communication out of convenience, potentially jeopardizing sensitive information. Another email of Clinton’s, released in January, appeared to show her telling a top aide to remove identifying details and send a sensitive document through a “nonsecure” channel instead of via "secure fax."

“This drip, drip of new Clinton emails show Hillary Clinton could not care less about the security of her communications,” said Tom Fitton, the president of Judicial Watch, in a statement releasing Thursday’s email. “How many other smoking gun emails are Hillary Clinton and her co-conspirators in the Obama administration hiding from the American people?”

Judicial Watch obtained the messages as part of a lawsuit filed against the State Department under the Freedom of Information Act.

The emails were not included in the more than 30,000 messages released by the State Department in recent months, raising questions about the scope of the department’s records.

Clinton’s presidential campaign has previously said the Democratic presidential front-runner did not use the personal “clintonemail.com” account during the early weeks of her time as the nation’s top diplomat. Instead, they have said, she used a different account, which was a holdover from her time as a senator, and she no longer has access to those emails.

The State Department’s publicly available cache of Clinton emails do not begin until March of 2009, weeks after she entered office.

The email released on Thursday was sent through a clintonemail.com account she used throughout the remainder of her time in office.

Judicial Watch has uncovered other emails of Clinton's through its lawsuit that were not released by the State Department.

In addition to the emails she gave to the State Department, Clinton withheld roughly 30,000 emails and deleted them from her private server. Those emails were purely personal in nature, she has claimed, and related to yoga routines, her daughter’s wedding and other unofficial matters.

Clinton’s server is currently in the hands of the FBI, which is investigating whether she or her aides mishandled classified material.