Chapman was still in prison when the
Channel Islands were invaded by the Germans in June 1940. Under the direction of Captain , head of the in
Nantes, he was trained in explosives, radio communications, parachute jumping and other subjects at
La Bretonnière-la-Claye, Saint-Julien-des-Landes, near Nantes, and dispatched to Britain to commit acts of sabotage. He was equipped with wireless, pistol, cyanide capsule and £1,000 and, amongst other things, was given the task of sabotaging the
de Havilland aircraft factory at
Hatfield in order to disrupt the production of the
de Havilland Mosquito aircraft. German reconnaissance aircraft photographed the site, and the faked damage convinced Chapman's German controllers that the attack had been successful. To reinforce this story, MI5 also wrote and had published a story in the British newspaper the
Daily Express. Following the de Havilland subterfuge, B1A began preparations for Chapman's return to his German handlers. Radio messages were sent to the Abwehr requesting extraction by boat or submarine, and Chapman was set to work learning a cover story ready for the inevitable interrogations. However, the response from the Abwehr was lukewarm. They refused to send a
U-boat and told Chapman to return via
Lisbon, Portugal. This was not a simple method, as he had no valid reason to travel to the neutral port. Reed, and other members of B1A, believed this demonstrated the Germans' reluctance to pay Chapman the £15,000 he had been promised. To get Chapman to Lisbon, it was decided he would join the crew of a merchant ship, and jump ship when it docked in Portugal. A fake identity, Hugh Anson, was constructed and the relevant paperwork was obtained before Chapman joined the crew of
The City of Lancaster, sailing out of
Liverpool. On making contact with Germans at their Lisbon embassy, he suggested an attempt at blowing up the ship with a bomb disguised as a lump of coal to be placed in the coal bunker. This was in response to a request from Britain's anti-sabotage section that he obtain examples of German explosive devices. He was given two bombs, which he handed to the ship's captain. The Germans did not notice the ship was not damaged on the voyage home, but to avoid the Germans' doubting Chapman's commitment, the British staged a conspicuous investigation of the ship when it returned to Britain, hoping that gossip about this would make its way back to the Germans. Chapman was sent to
occupied Norway to teach at a German spy school in
Oslo. After a debriefing by von Gröning, Chapman was awarded the
Iron Cross for his work in apparently damaging the de Havilland works and the
City of Lancaster, making him the first Englishman to receive such an award since the
Franco-Prussian War of 1870–71. suggests that as the Iron Cross was only ever given to military personnel, Chapman's "Iron Cross" may instead have been a War Merit Cross 2nd Class, or
Kriegsverdienstkreuz. Chapman was inducted into the
German Army as an
oberleutnant or first lieutenant. Chapman was also rewarded with and his own yacht. An MI5 officer wrote in an assessment "the Germans came to love Chapman ... but although he went cynically through all the forms, he did not reciprocate. Chapman loved himself, loved adventure, and loved his country, probably in that order". While in Oslo he also secretly photographed the German agents who stayed at his safe house.
Return to London After
Operation Overlord, he was sent back to Britain to report on the accuracy of the
V-1 weapon and the
Hedgehog antisubmarine weapon. He parachuted into
Cambridgeshire on 29 June 1944 and went to London. Here he consistently reported to the Germans that the flying bombs were hitting their
central London target, when in fact they were undershooting. Perhaps as a result of this disinformation, the Germans never corrected their aim, with the end result that most bombs landed in the
south London suburbs or the
Kent countryside, doing far less damage than they otherwise might have done. During this period he was also involved in doping of dogs in
greyhound racing and was associating with criminal elements in West End nightclubs. He was also indiscreet about the sources of his income and so MI5, being unable to control him, dismissed him on 2 November 1944. Chapman was given a £6,000 payment from MI5 and was allowed to keep £1,000 of the money the Germans had given him. He was granted a pardon for his pre-war activities and was reported by MI5 to have been living "in fashionable places in London always in the company of beautiful women of apparent culture". ==Love life==