Kennington was already a painter when he was invalided from the army in 1915, returning home to paint 'The Kensingtons at Laventie' (Imperial War Museum). In 1916, as an 'artist visitor' at the Front, he met Muirhead Bone, the first official war artist. T.E. Lawrence became a strong influence on him and he became art editor of 'Seven Pillars of Wisdom', for which he drew the portraits of Arabs.

In the Second World War he drew portraits of Chiefs of Staff and war heroes, many of which were published. He drew Dove in 1940, along with other seamen. Dove's badge indicates that he was a gunnery specialist.