Newly declassified NSA documents provide official confirmation that Edward Snowden was a CIA asset, and show the extent to which the government went to discredit him after he told lawmakers in Europe that he tried to blow the whistle on a secret federal program that snooped on private citizens.

The documents, obtained by Vice News, do not conclusively confirm claims by Snowden, then a private contractor working for the NSA, that he tried to alert supervisors of what he believed to be illegal spying before going public. They do show that following a flurry of claims by Snowden in early 2014 that his supposed concerns the agency was violating the constitutional rights of citizens were ignored, Obama administration officials sought to discredit him with his own words.

That effort centered around discussing the eventual May 2014 release of an April 2013 email from Snowden to the agency’s Office of General Counsel asking whether an Obama executive order allowing the snooping program could supersede federal statute. Officials largely viewed the query as simply a question about a test administered to contract workers.

“I’m not entirely certain, but this does not seem correct, as it seems to imply Executive Orders have the same precedence as law,” Snowden writes in the email after reposting a section of “the training.”

“My understanding is that EOs may be superseded by federal statute, but EOs may not override statute. Am I incorrect in this? Between EOs and laws, which have precedence?”

Snowden had contacted reporter Glenn Greenwald, who later used Snowden’s stolen NSA documents in several stories, four months before he wrote the email.

The email was forwarded to the Signals Intelligence Oversight and Compliance training group – the designers of the test – back to the OGC and then to two attorneys as the offices apparently sought to figure out who should answer the question. One of the lawyers ended up responding to Snowden.

“Executive Orders (E.O.s) have the ‘force and effect of law,’” the email said. “That said, you are correct that E.O.s cannot override a statute.”

The released documents contain no further written correspondence with Snowden regarding the issue. The files, however, do show a back-and-forth debate over the merits of releasing the Snowden email, a seemingly innocuous communication that does not appear to show an employee deeply troubled by domestic and foreign spying. The discussion centered on how NSA employees viewed the email, and how others might spin it.

Less than six weeks after he sent the April 2013 email, Snowden fled to Hong Kong with thousands of classified government documents. He is now in Russia.

“To the extent Snowden was saying he raised his concerns internally within NSA, no rational person could read this as being anything other than a question about an unclear single page of training,” Robert Litt, the general counsel of the Office of the Director of National Intelligence, told Vice News.

The newly released emails also provide the first official confirmation that Snowden worked with the CIA, Vice News reported. An email from the NSA to all agency employees sent on June 10, 2013, identified Snowden as a “current NSA contractor and former CIA affiliate.”