The State Department narrowly missed a court-ordered deadline on Monday to release documents about whether former Secretary of State Hillary Clinton Hillary Diane Rodham ClintonJoe Biden looks to expand election battleground into Trump country Biden leads Trump by 12 points among Catholic voters: poll The Hill's Campaign Report: Biden goes on offense MORE and her senior aides participated in security training and briefings.

An email mix-up prevented an Obama administration lawyer from sending hundreds of pages of material to the Daily Caller News Foundation, an investigative reporting arm of the conservative-leaning website.

The State Department tried to send 8.4 megabytes worth of documents at 7:58 p.m. on Monday evening, it claimed in a court filing on Tuesday morning.

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“The size of the file attached to the email, however, exceeded the maximum file size allowed for the mobile device used by counsel for State, and thus transmission of the email did not complete,” the department asserted. “Counsel for State was unaware of this fact until this morning, September 27, 2016.”

When the State Department’s legal team realized what happened, it sent a second email from another mobile device containing the government records. The second email was sent at 7:45 a.m., nearly eight hours after the midnight deadline.

“Counsel for State also contacted counsel for plaintiffs via phone, explained what had occurred, and apologized for the error,” the department said.

Screenshots submitted to the federal court show that the lawyer received but apparently did not notice a notification that the email was “too large” to send.

The delay is an embarrassing one for the State Department, which has struggled under the weight of dozens of open-records lawsuits and thousands of document requests.

Last week, Judge Richard Leon of the District Court for the District of Columbia demanded that the department have until Monday to release one-third of the roughly 400 documents showing whether Clinton and her senior aides were informed about the need to protect classified material. Subsequent releases were ordered out by Oct. 3 and Oct. 10.

The lawsuit stems from questions about Clinton’s efforts to safeguard sensitive material through the use of her private email system. FBI Director James Comey has testified in Congress that Clinton, now the Democratic nominee for president, might not have been “sophisticated enough” to understand classification markings.