She is the author of The Unravelling: High Hopes and Missed Opportunities in Iraq (2015) and In a Time of Monsters: Travelling in a Middle East in Revolt (2019).

[2][5][7][8] Sky served in 2005 in Jerusalem as the Political Advisor to General Kip Ward, the US Security Co-ordinator for the Middle East Peace Process.

In 2006, she was based in Kabul, Afghanistan as the Development Advisor to the Italian and British Commanding Generals of NATO's International Security Assistance Force.

[4] Since August 2012, Sky has been a Senior Fellow at the Yale Jackson School of Global Affairs, where she lectures on Iraq and Middle East politics.

Sky oversaw the transition of the program to the Jackson Institute for Global Affairs,[14] and in 2016 secured a $16 million contribution from the Starr Foundation and Maurice R.

[18] In 2019 Sky’s “Middle East Politics” class at Yale was the first subject of a string of campus protests called “Do You Trust Your Educator?” by Zulfiqar Mannan and 4 other Yale students as part of “Paradise Sought” a larger capstone project inspired by ‘gaga-feminism’ and David Scott Kastan’s 2005 edition of John Milton’s ‘Paradise Lost’.

Her book - a collection of personalised travel writing in Egypt, Tunisia, Syria, Iraq, Turkey, Saudi Arabia, Oman, Kurdistan, The Silk Road, Jordan, The Balkans and Britain over the period 2011-2016 - makes no further reference to Gramsci’s works (even though in ‘State and Civil Society’ he goes on to mention ‘the so-called “problem of the younger generation” - a problem caused by the “crisis of authority” of the old generation in power, and by the mechanical impediment that has been imposed on those who could exercise hegemony, which prevents them from carrying out their mission.’ (op cit).)