A federal judge on Friday dismissed a lawsuit against Obama administration officials for the 2011 drone strike killings of three U.S. citizens in Yemen.

U.S. District Judge Rosemary Collyer said that the case raises serious constitutional issues and is not easy to answer, but that based “on these facts and under this circuit’s precedent,” the court will grant the administration’s request.

U.S.-born Anwar al-Awlaki, a leader or al-Qaeda in the Arabian Peninsula (AQAP), and Samir Khan, an AQAP propagandist, were killed in a drone strike in September 2011. Al-Awlaki’s 16-year-old son, Abdulrahman, was killed in a strike the following month.

The lawsuit was filed by Nasser al-Awlaki – Anwar’s father and the teen’s grandfather – and by Sarah Khan, Samir Khan’s mother.

The suit was against then-Defense Secretary Leon Panetta, then-CIA Director David Petraeus and two commanders in the military’s Special Operations forces.

Permitting a lawsuit against individual officials “under the circumstances of this case would impermissibly draw the court into the ‘heart of executive and military planning and deliberation,’” Collyer said.

In oral arguments last July, the judge challenged the Obama administration’s position repeatedly, asking “Where was the due process in this case?” for the now-dead U.S. citizens targeted in the attacks.

When an administration lawyer said there were checks in place, including reviews done by the executive branch, Collyer said, “No, no, no, no” and declared that “the executive is not an effective check on the executive” when it comes to protecting constitutional rights.

But in Friday’s ruling, the judge – appointed by former President George W. Bush – made was clear that the administration’s argument had a strong impact on her. She said that the U.S. government moved against al-Awlaki as authorized by the defendants, and that the officials acted in accordance with the Authorization for Use of Military Force – enacted by Congress after the attacks of Sept. 11, 2001.

Al-Awlaki had been linked to the planning and execution of several attacks targeting U.S. and Western interests, including a 2009 attempt on Christmas Day on a Detroit-bound airliner and a 2010 plot against cargo planes.

"The fact is that Anwar al-Awlaki was an active and exceedingly dangerous enemy of the United States, irrespective of his distance, location, and citizenship," Collyer said. "As evidenced by his participation in the Christmas Day attack, Anwar al-Awlaki was able to persuade, direct and wage war against the United States from his location in Yemen, without being present on an official battlefield or in a hot war zone."

The Associated Press