The State Department missed by hours a federal court-ordered deadline on Monday to hand over hundreds of documents related to Hillary Clinton’s participation in required security training during her tenure as secretary of state.

An Obama administration attorney said technical delays prevented the department from sending the material to the Daily Caller News Foundation until 7:45 a.m. Tuesday, nearly eight hours after the midnight deadline, the Hill reported.

The State Department said in a court filing on Tuesday morning it attempted to send a trove of documents Monday evening, but the email failed to go through.

"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 wrote. "Counsel for State was unaware of this fact until this morning, September 27, 2016."

The administration attorney received a notification that the email was "too large" to send, but did not see the alert, according to screenshots from the State Department.

Judge Richard Leon rejected the State Department’s motion last week to dismiss a Freedom of Information Act lawsuit brought by the Daily Caller News Foundation seeking to confirm that Clinton and her top aides underwent mandatory annual security briefings regarding the proper handling of classified materials and best practices to ensure secure communications.

The State Department has so far refused to produce such records and concluded in July that the delay meant the "courses were not completed" by Clinton or her aides, including former chief of staff Cheryl Mills and deputy chief of staff Huma Abedin.

Leon ordered the department to release a third of the 400 documents requested by Sept. 26, while the rest must be handed over by Oct. 10.