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Clinton had often said that she never handled anything \"marked\" classified at the time it was originally sent or received. That statement appears to be true. But it's not possible to send a properly marked and classified email through an unclassified State Department account or a private email account, according to multiple senior government officials familiar with handling sensitive materials in the government email system.

It is possible, however, to quote from a classified email and send that through an unclassified system, which unless reported by the sender or receiver would not be detected until a later review.

One email released tonight demonstrates that at least one member of the State Department’s “Help Desk” was unaware that Secretary Clinton was using a private email address.

State Dept. IT Help Desk sends email to #Clinton's private address on her server, not knowing who she was. pic.twitter.com/vsrUlkae1T

— Justin Fishel (@JustinFishelABC) September 1, 2015

On Saturday, February 27, 2010 a help desk analyst named Christopher Butzgy sent an email to HDR22@clintonemail.com, unaware that he was communicating with the Secretary of State. He informed her that one of his customers had been “receiving permanent fatal errors from this address.”

Secretary Clinton forwarded the email to her aide and advisor Huma Abedin asking, “Do you know what this is about?”

“Ur email must be back up!!,” Huma replied, before explaining that the error messages prompted a staffer to get State Department Help Desk involved. “They had no idea it was YOU, just some random address so they emailed,” Abedin wrote.

Republican front-runner Donald Trump has repeatedly compared Clinton's email scandal to that of retired CIA Director, Gen. David Petraeus, who earlier this year plead guilty to a misdemeanor charge of mishandling classified information. He was originally charged with a felony, but pleaded guilty to a lesser charge in a deal with the prosecution.

One of those prosecutors penned a story in USA Today Sunday evening, claiming that Trump is making a false comparison. Anne Tompkin describes herself as the former US attorney for the Western district of North Carolina and said she oversaw the prosecution. \"The key element that distinguishes Secretary Clinton’s email retention practices from Petraeus’ sharing of classified information is that Petraeus knowingly engaged in unlawful conduct, and that was the basis of his criminal liability,\" Tompkin wrote. The USA Today also noted that Tompkin has donated to Clinton's presidential campaign.

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