Outgoing Joint Chiefs of Staff Chairman Gen. Martin Dempsey admits in a new interview that the U.S. military had done no contingency planning to prepare for the fall of Mosul when Islamic terrorists swept into Iraq’s second-largest city last June and seized control.

“Well, no, there were not,” Dempsey replies in the interview with Frontline’s Martin Smith when asked if there were any contingency plans inside the Pentagon for how to respond if Mosul were to fall to terrorists from the Islamic State (or ISIL, as the group is sometimes called.)

“So, look, there were several things that surprised us about ISIL,” Dempsey adds. “The degree to which they were able to form their own coalition, both inside of Syria — and inside of northwestern Iraq; the military capability that they exhibited — the collapse of the Iraq Security Forces. Yeah, in those initial days, there were a few surprises.”

Dempsey’s frank comments would appear to raise fresh questions about the performance of U.S. intelligence agencies in tracking the rise of IS as well the state of planning inside the Obama administration as it continues to grapple with a war against the Islamic State terrorists.

John Maguire, a former senior CIA officer in Iraq, called Dempsey’s remarks “stunning” and described his admission of the failure to do any planning as comparable to the intelligence failures prior to the Sept. 11 terror attacks. He noted that Islamic State terrorists had been on the march inside Iraq for months before Mosul was attacked and that IS had already seized huge swaths of territory, including the city of Fallajuh, the previous January.

“Good lord, he should resign,” Maguire told Yahoo News, when read a transcript of Dempsey’s comments for the Frontline show, “Obama at War,” which airs Tuesday night on PBS.

“The highest ranking military officer in the country is surprised by an issue that has been percolating for over a year?” said Maguire, who now serves as an advisor to the Kurdish forces battling the Islamic State. “That is breathtaking. Where in hell is the Central Intelligence Agency? We’ve got a $75 billion intelligence budget. There is no excuse for this.”

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Dempsey is not the first senior official to acknowledge that U.S. intelligence officials and the White House itself missed the ferocity of IS’s advance. President Obama, in an interview with the New Yorker in January, 2014, referred to IS as the “jayvee,” as in a junior varsity athletic team. And Director of National Intelligence James Clapper acknowledged last September that U.S. intelligence officials underestimated” IS and the ability of the Iraqi Army to fight back against the terrorists.

“I didn’t see the collapse of the Iraq security force in the north coming,” Clapper told Washington Post columnist David Ignatius in a Sept. 18, 2004, interview. “I didn’t see that.”

But Dempsey’s remarks would appear to take the issue to a new level by admitting the lack of any “worst case scenario” planning inside the Pentagon despite months of warnings from some U.S. intelligence officials that IS was advancing rapidly through northern Iraq and Syria. “ISIL probably will attempt to take territory in Iraq and Syria in 2014, as demonstrated recently in Ramadi and Fallajuh,” Lt. Gen. Michael T. Flynn, then the director of the Defense Intelligence Agency, stated in an annual “threat assessment” report to Congress on Feb. 14, 2014.

Smith, the Frontline correspondent who conducted the interview with Dempsey, said he, too, was taken aback by the general’s comments, noting the Pentagon routinely does contingency planning for all sorts of scenarios. “I can’t explain it,” said Smith about Dempsey’s comments. “We had invested how many billions in the Iraqi Army? It’s something you would think they would keep an eye on. Yet they seemed entirely blindsided.”

Underscoring just how blindsided officials were, are comments in “Obama at War” from another former senior Pentagon official.

“The fall of Mosul was something that we had not anticipated,” Derek Chollet, the former assistant secretary of defense for international security affairs, says in the film. “And the suddenness with which that fall occurred was something that — that was a shock. They seized everything from small arms to light-armored vehicles- to anti-aircraft weapons. When terrorists of this kind get their hands on weapons, it was a huge concern to us. I don’t think we truly understood the depth of the problem until the fall of Mosul.”

Today, nearly a year later, Mosul — a city of more than one million — remains firmly under IS control and the Iraqi government, working closely with the U.S. military, has pushed back plans to retake the city.

The Frontline film reviews the Obama White House’s efforts to grapple with the mounting crisis in Iraq and Syria during a time it was attempting to withdraw U.S. troops from the region.

In another part of his interview with Smith, Dempsey describes how the Pentagon was “on the trigger,” ready to launch military action against the regime of Syrian President Bashar al-Assad in 2013 after U.S. officials had concluded he had launched a sarin gas attack against a rebel holdout in a suburb of Damascus, thereby crossing a “red line” that the president had publicly said he would not permit.

The consensus was that the Pentagon would launch strikes in Syria on Saturday, Aug. 31, Smith reports in the film.

“Our finger was on the trigger,” Dempsey says in the film. “We had gone through the targeting plans and the targeting solutions. The crews were alerted. And so we had everything in place and we were just waiting — for instructions to proceed.”

But then after the British House of Commons voted not to support the action, Obama began to pull back.

“It was a Friday night and I got a call from the president of the United States,” Dempsey reccalls. “And he said to me, ‘I am considering an alternative course of action.’ And he wanted me, overnight, to consider whether a delay would, in any way, affect our ability to be effective with our military options.”