He subsequently served as Deputy Governor in Maysan and Dhi Qar for the Coalition Provisional Authority following the 2003 invasion of Iraq and wrote a second book covering this period, Occupational Hazards or The Prince of the Marshes.

On 3 September 2019, Stewart had the Conservative Whip removed after voting to back a motion paving the way for a law seeking to delay the UK's exit date from the European Union.

[5][17] In Indonesia, he served as the Political & Economic Second Secretary in the British embassy in Jakarta from 1997 to 1999, during the Asian Financial Crisis and the fall of Suharto, working on issues related to East Timor independence.

[7] Some have suggested that Stewart was an employee of the Secret Intelligence Service (MI6) during his time as a British Representative to Montenegro – allegedly being recruited to MI6 shortly after he graduated from the University of Oxford.

[20] A former aide to Seema Kennedy reported that, as an MP, Stewart climbed out of her fifth-floor window in the Norman Shaw Buildings to enter his locked office next door despite the outside wall being bare; "[t]o this day I have no idea how he managed to do it".

[23] While Stewart initially supported the Iraq War, the international coalition's inability to achieve a more humane, prosperous state led him in retrospect to believe the invasion had been a mistake.

Stewart was awarded the Royal Scottish Geographical Society's Livingstone medal in 2009 "in recognition of his work in Afghanistan and his travel writing, and for his distinguished contribution to geography".

[33] According to The Daily Telegraph, Brad Pitt bought the rights to make a film about Stewart in 2008, with Orlando Bloom tipped to play the leading role.

[7] The New York Times critic William Grimes commented that for him the "real value of the new book is Mr. Stewart's sobering picture of the difficulties involved in creating a coherent Iraqi state based on the rule of law".

A personal account of Stewart's years in politics, starting with his attempts to be selected as a Member of Parliament, it describes his experiences as an MP, as a junior and then a senior minister, and his Conservative leadership bid.

[53] In 2014, Stewart wrote and presented a two-part documentary on BBC Two about the cross-border history of what he called "Britain's lost middleland",[54] covering the kingdoms of Northumbria and Strathclyde and the Debatable Lands of the Scottish Marches on the Anglo-Scottish border.

[56] In late 2005, Stewart set up the Turquoise Mountain Foundation in Afghanistan, a human development NGO established by King Charles III and Hamid Karzai.

[57] For this role he relocated to Kabul for the next three years, working to restore historic buildings in its old city, managing its finances, installing water supply, electricity, and establishing a clinic, a school and an institute for traditional crafts.

[59] In 2021, Stewart and his family moved to Jordan for two years to work for the Turquoise Mountain Foundation, setting up a project to restore a Roman site near the Golan Heights to create employment in the area.

[7] In an article in The Daily Telegraph, he was described as an advisor on Afghan issues to U.S. Secretary of State Hillary Clinton, and the U.S. Special Envoy for Afghanistan and Pakistan Richard Holbrooke.

[66] In September 2020, he became a fellow at Yale University's Jackson Institute for Global Affairs, teaching politics, grand strategy and international relations to undergraduate and graduate students.

[104] In January 2014, Stewart was asked by Chris Grayling, Secretary of State for Justice, to lead a government review into the reasons why a number of British veterans become criminal offenders after returning to civilian life.

During the run up to the Scottish independence referendum,[115] Stewart said of the project: "We wanted to come up with a lasting marker of our union, something that future generations will look back at and remember, with deep gratitude, the moment we chose to stay together.

"[116] The campaign received support from several notable public figures in the UK, including actress Joanna Lumley, explorer Sir Ranulph Fiennes, mountaineers Alan Hinkes and Doug Scott, and historians Simon Schama and David Starkey.

[121] The House of Commons cross-party Environment Audit Committee criticised the statement by Stewart that the extra £700m for flood defence was the result of a "political calculation" and that it might not be spent according to the strict value-for-money criteria currently used.

[144] He was appointed in the aftermath of a highly critical leaked report on the state of HMP Liverpool, in which the inspector described it as the "worst prison he had ever seen" with piles of rubbish, rats, soaring violence and drug use and poor health provision.

[146] This advocacy of a "back to basics" approach was recorded in The Guardian, with Stewart writing an opinion piece entitled "I strongly believe we can improve our prisons and make progress".

[citation needed] Other international visits took Stewart to environmental programs in Kenya (from wind turbine projects in Lake Turkana in the north to Mangrove Protection in Lamu on the east coast), and UK aid funded programmes in Jordan (holding meetings with Prime Minister Omar Razzaz).

[161] Adopting an unconventional campaigning style, Stewart did not focus his attention on Westminster but, instead, went on a series of filmed walkabouts (dubbed 'RoryWalks'), which saw him take to the streets of Britain, talking to voters, to understand their priorities and concerns.

[171] However, in his podcast with co-host Alastair Campbell, Stewart claimed that Gove was intentionally wasting his time in order to better position Boris Johnson in the leadership race.

The next day, Stewart confirmed his resignation on Twitter, saying: "It's been a great privilege to serve Penrith and The Border for the last ten years, so it is with sadness that I am announcing that I will be standing down.

He is often aligned with the moderate wing of the Conservative Party and has expressed distaste towards subsequent prime ministers, Boris Johnson and Liz Truss, although was generally supportive of Rishi Sunak's tenure.

"[194] Before the 2024 United States presidential election, despite most polling suggesting the contest was extremely close, Stewart predicted that Kamala Harris would "win comfortably" against Donald Trump.

He continued to argue, following that defeat, that following the outcome of the referendum "the Customs Union option was the best available – the only way of achieving the substantial separation desired by Brexit voters while remaining close to the EU diplomatically and economically.

"[206] He proposed, however, following the failure of parliament to reach any positive agreement – that the issue could be passed to a citizens' assembly, chaired by the Archbishop of Canterbury to find a compromise on Brexit.