An unpaid bar bill, a blocked request to visit frontline troops and a thwarted Jaguar joyride are among diplomatic headaches revealed in email exchanges about a trip to Iraq by Boris Johnson last year.
The Mayor of London travelled to Kurdistan a year ago, at the invitation of Kurdish prime minister Nechirvan Barzani, to see UK troops training Peshmerga fighters taking on the self-styled Islamic State.
It was widely viewed as an attempt to bolster his credentials as a possible future prime minister and a photograph of him peering along the sights of a gun ensured it received much media coverage.
But 200 pages of email exchanges between diplomats, the Foreign Office, City Hall and others, released under the Freedom of Information Act, have laid bare some of the behind-the-scenes wranglings.
One "sensitive" issue raised by the FCO related to "costs relating to alcohol purchases ... that we might have to charge to the Mayor's office".
It notes that "clear instructions were giving to the party that purchases of alcoholic drinks must be paid in cash and not charged to rooms".
The mayor's spokesman put the failure to settle the "private" hotel tab down to "an administrative oversight" and stressed that Mr Johnson had paid it from his own pocket when it was pointed out.
Another exchange shows that Downing Street initially blocked a request for the mayor to visit troops but later "softened" their position "from 'no' to 'as long as it's done in an appropriately sombre manner'".
The idea of him going to the front line however caused serious concerns - especially when Mr Johnson was apparently unwilling to take no for an answer.
In an email titled "out of area move", Angus McKee, the UK's Consul General to the Kurdistan Region & Northern Iraq, said: "The visiting Mayor said he would like to visit the 'front line'.
"I explained that was not possible, we never went etc. He is not satisfied."
He asked for confirmation that there was "no viable trip to the frontline in the proximity of Erbil" and that then FCO Middle East director Edward Oakden - now the UK's ambassador to Jordan, "has zero appetite" to authorise such a trip.
He was told it was "safe to say that Edward will indeed have zero appetite for this".
"Not for the Mayor, but it's probably also something we'd have to clear with No.10," he was told.
The emails also shed more light on an incident - reported at the time by the Mail on Sunday - that the mayor "hit the gas and roared off" after being invited to sit behind the wheel of a new F-Type Jaguar in a car showroom in Erbil.
"In case anyone gets alarmed by the attached article," Mr McKee wrote afterwards.
"While it is true that the Mayor got behind the wheel .. in the showroom, drove out of the door and onto the driveway, quick action by his PPO (protection officer) and me ensured he did NOT drive off."
There are also negotiations over the mayor's desire to see the historic sights and "include some time in a bazaar / do some shopping" - with diplomats explaining that extending leisure opportunities might be "tricky".
Officials are also recorded expressing frustration over a last-minute decision by Mr Johnson that he wanted to visit a refugee camp.
"I have no objection to this locally, however I know there has been some politics between No10, MOD and the Mayor's Office over what he can and can't do here," one email says.
When it is suggested that the Department for International Development could veto the trip if they were unhappy, an unnamed DfID official said: "I can't see how we could pull it even if we wanted to as he is on his way."
The emails show that the mayor's office sought business class flights for his party, worrying that the Kurdish PM's office - which was paying most of the costs of the trip - "don't think our request is too cheeky or onerous".
In the end a private plane was supplied instead.
The FCO said it paid only £10.59 for travel and £136.83 for "other expenses (meals, telephone, tea and coffee)".
At one point during preparations for the trip, there was a discussion about whether or not local regional sensitivities meant Mr Johnson should avoid mentioning Winston Churchill while there.
"In one-to-one conversations with leading Kurds, there is a lot of admiration for Churchill's leadership and historic role," an official concluded.
"Speaking to audiences and with the media, we recommend Churchill is not mentioned."