In July 1940, Jackson was commissioned to make six portrait drawings, at 10 guineas each. These included drawings made at the Royal Ordnance Factory at Irvine, and the Royal Gunpowder Factory, Waltham Abbey. A further three drawings were commissioned in November the same year (19), and in November a portrait of Major General Taylor of the bomb disposal organisation, but this commission was later abandoned as a "failure". In April 1941, five further portraits were commissioned, of naval subjects (43, 46) and two Home Security subjects in February 1942 (64). A portrait of General Nye was discussed but was eventually declined by Jackson.
Further commissions were offered in March 1944 (7 drawings) and April 1944 (2 admiralty drawings), although there is no mention of these being completed. In September 1944 an oil portrait was commissioned, for 50 guineas. Note that the original subject of this picture was not the final one.
The remainder of the file comprises correspondence with and about Jackson's estate, after his death in 1945, and a portrait photograph of him (118); and correspondence regarding a memorial exhibition of his work.