The U.S. Supreme Court has turned down the appeal of a prominent journalist seeking to avoid testifying in a leak case. The move effectively placed the U.S. Supreme Court on the side of the Obama administration, which has been aggressive in going after journalists it accuses of publishing classified information.

The journalist at the center of the case is New York Times writer James Risen, who in March called the Obama administration “the greatest enemy of press freedom that we have encountered in at least a generation.” The U.S. Supreme Court has now given the administration more leeway to prove Risen’s point with a decision that rejected the reporter’s argument that he should not be compelled to reveal a source.

Since May 2011, Risen, an investigative journalist working on national security issues, has been in the crosshairs of the Obama administration over his 2006 book, State of War: The Secret History of the C.I.A. and the Bush Administration. The U.S. subpoenaed Risen, telling him he must testify in the case of former CIA employee Jeffrey Sterling, who is accused of leaking classified information that ended up in Risen’s book. The classified information Risen wrote about concerned a CIA effort to scuttle Iran’s nuclear energy program by employing a former Russian scientist. The scientist is said to have given Iran a blueprint for a nuclear triggering device that had a design flaw.

Risen has fought back, saying he would go to jail rather than reveal a source. He appealed all the way up to the Supreme Court. But on Monday, the highest court turned down Risen’s appeal, which was a last-ditch effort to defeat a U.S. Court of Appeals order that Risen testify in Sterling’s case. Now, a showdown over Risen’s refusal to reveal his source, and the larger issue of press freedom, will take place at an appeals court in Virginia.

While Attorney General Eric Holder recently pledged that under his watch, journalists will not go to jail, the administration has continued to use the judicial system to harass journalists into revealing their sources. Journalists and press freedom advocates say the administration’s war on journalists has chilled national security reporting, with potential sources afraid to speak to reporters for fear of being prosecuted. Here are four other cases where the Obama administration has targeted journalists.

1. James Rosen

Rosen (a different person than James Risen) is a Fox News reporter who was labeled a potential criminal by the Obama administration over his 2009 reporting on North Korea. That year, he published an article reporting that North Korea was about to conduct a nuclear weapons test.

The Justice Department started to investigate Rosen and ultimately indicted Stephen Jin-Woo Kim, a State Department contractor said to have given Rosen the information he used in his article. The government charged Kim with violating the Espionage Act, a World War I-era law that has been a favored tool of the Obama administration in its attacks on journalists and sources.

While Rosen has not been charged, he has faced other government accusations and harassment. Rosen’s phone and e-mail records were seized during the investigation of Kim. The FBI also used electronic security badge records to track when Rosen and Kim met. And finally, the U.S. claimed “there is probable cause to believe that the reporter has committed or is committing a violation” of the Espionage Act. The evidence? Rosen played to Kim’s “vanity and ego” while trying to elicit information about North Korea—something journalists often do as part of their jobs.

2. Matt Apuzzo and Adam Goldman

The tag-team national security reporting duo’s stories have sparked three investigations since Obama took office. Apuzzo’s and Goldman’s stories for the Associated Press have raised the ire of the U.S. government, though Apuzzo has moved on to the New York Times, with Goldman now working for the Washington Post.

The Obama administration has looked into the sources for stories concerning al Qaeda plots in New York and Norway, but the most egregious efforts by the U.S. government were revealed last May. Apuzzo and Goldman revealed that the CIA had disrupted an alleged Al Qaeda in the Arabian Peninsula plot to blow up an airliner on the one-year anniversary of the death of Osama bin Laden. The Justice Department wanted to find out who their source was for the reporting so they seized Apuzzo’s and Goldman’s phone records. The department also seized the phone records of other reports and editors on the story.

“There can be no possible justification for such an overbroad collection of the telephone communications of the Associated Press and its reporters,” Gary Pruitt, the president of the Associated Press, wrote in a letter to Attorney General Holder. “These records potentially reveal communications with confidential sources across all of the newsgathering activities undertaken by the AP during a two-month period, provide a road map to AP’s newsgathering operations and disclose information about AP’s activities and operation that the government has no conceivable right to know.”

3. Mike Levine

The latest revelation of a journalist being targeted was published last week by the New York Times’ Charlie Savage, who revealed that a former Fox News reporter, Mike Levine, was subpoenaed in 2011.

Levine, now working for ABC News, reported a story revealing that a grand jury had secretly indicted three Somali-Americans suspected of going to fight with al-Shabaab, an Islamist extremist group in Somalia the U.S. has been battling. Levine made the revelation even though court records were supposed to be sealed.

The U.S. government then subpoenaed Levine for his notes and wanted him to testify in their investigation over who leaked the information to Levine. He fought the U.S. over the subpoena rather than comply with it, and the Justice Department dropped the case in 2012.

4. Glenn Greenwald and Laura Poitras

Greenwald and Poitras are the two journalists most closely associated with the Edward Snowden leaks. The duo were picked by Snowden to report on the National Security Agency documents he spirited away to Hong Kong.

There is no known U.S. investigation of the two related to the Snowden leaks. But the U.S. government has implied that both were “accomplices” in the Snowden leaks, and Poitras has run into her own trouble at U.S. borders.

During a January 2014 Senate hearing, National Intelligence director James Clapper said, “Snowden claims that he’s won and that his mission is accomplished. If that is so, I call on him and his accomplices to facilitate the return of the remaining stolen documents that have not yet been exposed, to prevent even more damage to U.S. security.”

But U.S. authorities have gone beyond lobbing rhetorical bombs at Poitras, a filmmaker who has made documentaries on the impact of the U.S. war on terror. As Greenwald reported in 2012, Poitras has been stopped and detained at U.S. airports by Department of Homeland Security agents who interrogate her at length about her sources. U.S. authorities have also seized her laptop and cameras for weeks on end. While the harassment of Poitras began during the Bush administration, it has continued since Obama was elected.