At the International Society in April 1914 Kennington exhibited a series of paintings and drawings of costermongers which sold well and allowed him to set up a studio off Kensington High Street in London.

Kennington was injured while attempting to clear a friend's jammed rifle and he lost one toe and was fortunate not to lose a foot due to infection.

Later during this tour, his friend William Rothenstein was also appointed as a war artist and they worked together at Montigny Farm and at Devise on the Somme, where they often came under shell-fire.

Although Kennington was among the first of the official war artists Britain sent to France, he was not afforded anything like the status and facilities that the others, in particular William Orpen and Muirhead Bone enjoyed.

[11][12] Throughout June and July 1918 an exhibition of Kennington's work, "The British Soldier", was held in London and received great reviews and some public acclaim.

Despite this, Kennington was unhappy in his dealings with Department of Information, mainly concerning the censoring of his paintings, and he resigned his war artist commission with the British.

Kennington spent the first half of 1921 travelling through Egypt, Jordan, Syria, Lebanon and Palestine drawing portraits of Arab subjects.

In 1922 Kennington began to experiment with stone carving and soon undertook his first public commission, the War Memorial to the 24th Division in Battersea Park which was unveiled in October 1924.

These included the original dust jacket design for George Bernard Shaw's book The Intelligent Woman's Guide to Socialism and Capitalism.

Alongside Richard Carline, Leon Underwood and others he worked in a section attached to the Air Raid Precautions Department of the Home Office until war broke out.

The sitting took place on the afternoon of 7 September 1940 at the Air Ministry building in London and was interrupted by an air-raid siren which, after Learoyd had looked outside to see where the German planes were heading, the two men ignored.

[16] Kennington next spent some time at Bomber Command bases in Norfolk before moving to RAF Ringway near Manchester where the Parachute Regiment were training.

[10] Kennington continued to travel around Britain to produce hundreds of portraits of Allied flight crew and other service personnel until September 1942 when he resigned his commission because he felt that WAAC were failing to capitalise on the propaganda value of his work in their publications and posters.

Kennington resolved to create a suitable memorial for them and over the next ten years, whilst also working on sculpture and portrait commissions, he patiently carved 1940, a column with the head of an RAF pilot topped by the Archangel Michael with a lance slaying a dragon.

[21] His last work, which was completed on his death by his assistant Eric Stanford, was a stone relief panel that decorates the James Watt South Building in the University of Glasgow.