He only learned of his own schedule hours ahead of time, and the meeting with Kim Jong Un never happened - despite strenuous efforts from his staff.
The trip reflects the difficulty for Pompeo in dealing with one of the world's most reclusive and unpredictable regimes, which can shift from threats to warm words and back again at speed.
It comes as pressure mounts on him to show progress on the delicate task of getting North Korea to move forward on nuclear disarmament, including the issue of verification, and make good on US President Donald Trump's claimed accomplishments from the Singapore summit.
Amid talk of goodwill and Trump's repeated tweets of the bond he has developed with Kim, it was also a jarring reminder that North Korea's approach may not have changed as much as US officials - and Pompeo in particular - had hoped.
The US is seeking to persuade the world the North Koreans are genuinely prepared to give up the weapons they have developed in the face of years of false starts and broken promises to successive US administrations.
From the moment Pompeo landed in Pyongyang, North Korean officials quickly asserted control. Kim Yong Chol set the optics during their first meeting, which took place around a long wooden table in one of the many conference rooms off the carpeted hallways of the guesthouse complex.
Normally, media handlers from the host country would let reporters witness the first 30 seconds or so of such a meeting. But Kim's staff allowed reporters to stay for several minutes.
"The more you come, the more trust we can build between one another," Kim said.
Pompeo, who has yet to gain a taste for such theater, murmured a few pleasantries but quickly lost patience and called on Nauert to usher all media - North Korean reporters included - from the room.
Between the many hours of talks, the North Koreans sought to put forward an image of bounty and wealth, an alternate reality in a country where much of the population lives in hunger, lacks electricity and has little to no access to the internet or foreign television.
In the guesthouse, each room had bowls of bananas, grapes, oranges and pears that were replenished whenever the occupant was out. The internet speed was fast in each room and the BBC played on flat-screen televisions. In a country laden with the iconography of Kim Il Sung and Kim Jong Il, there were no portraits of either man in the compound.
Still, the reminders were there. Guests could roam the grounds and walk a path that surrounded a lake, but were blocked from approaching workers erecting a building nearby. Guards watched surreptitiously from behind a stand of trees.
The lack of US control clearly rankled Pompeo. A former military officer accustomed to short, focused meetings, he was made to sit through multi-course meals with Kim and his staff, as waiters brought plate after plate of food - foie gras, turkey, pea soup, boiled oak mushrooms, kimchi, watermelon and ice cream, plus a drink branded "American Cola."
By the morning of his second day, Pompeo had enough. Instead of the elaborate breakfast prepared for him, he ate toast and slices of processed cheese.
Despite the lack of progress, the North Koreans showed a keen awareness of broader politics in the US under Trump. On the way from the airport, riding in a Dodge Ram van, a minder was noncommittal about what the talks might bring.
"We'll have to see, like your president says," he said. He paused and added: "In this van, no fake news?"
The specifics of what happened behind closed doors remain unclear. Whether Pompeo somehow annoyed his counterpart, or pressed too hard, or whether the North Koreans are simply reverting to their hot-and-cold tactics, is hard to say. But the regime made sure to have the final word, and it was not pleasant.
As he was leaving, Pompeo told reporters the conversations were "productive and in good faith." Hours later North Korean state media issued a statement that did not mention him by name but called the demands he presented "gangster-like."
Days before the trip began, reporters travelling with Pompeo had to rush to get new passports with a special endorsement allowing entry to North Korea. In the end, authorities in Pyongyang never stamped them and the documents were returned unblemished. It was as if the secretary had never visited at all.
- Bloomberg