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From the start of the way on September the 9th of 1939, to May the ninth of 1940, little changed on the channel islands. Conscription did not exist. The horticulture and tourist trades continued as normal; with many tourists and service men on leave, being able to travel to the islands for some much needed rest and relaxation. However, This changed when on May the tenth, the Germans invaded France and the low countries. Airbases on the islands were used to conduct attacks on German forces, and later Italian towns when Italy joined the war in Early June.

With the Allied defeat in France in mid June, the channel islands were not deemed strategic enough to defend by the British government, so preparations for troops evacuation was ordered for the 20th. Even still, boats from the islands were used to evacuate troops from the French mainland, but they were to not stay for long. The Channel Islands had been demilitarized and declared an open town by June the 15, however, the statement was not made public, as the British government did not want to invite the Germans to take the islands. The channel governments were left in pretty much utter chaos, as they weren't able to get much in the way of straight answers from the mainland government, and each were essentially left to do whatever actions they decided to take. The authorities in Alderney, having no direct communication with the UK, recommended that all islanders evacuate, and all but a handful did so. In Sirk, it was encouraged that everyone was to stay. Guernsey evacuated 80% of children that were of school age, giving the parents the option of keeping their children with them, or evacuating them with their school. Due to the influx of people that aimed to leave, the official message turned to one of staying the following days. In total, 5,000 school children and 12,000 adults out of 42,000 were evacuated from the island. In Jersey, only around 6,000 out of 55,000 were evacuated.

The Germans did not realize that the islands had been demilitarized, as it wouldn't be made public until June 30th. so they approached with caution. Reconnisonse flights proved to not garner much information, but, some carts that were loaded with tomatoes, were mistaken as troop carriers in St. Peter Port, the main town of Gurneys, and the surrounding area got bombed, resulting in a total of 44 civilian deaths. The Wehrmatch drew up plans to invade the islands with two assault battalions, However, a luftwaffe reconnaissance pilot, Captain Liebe-Pieteritz, made a landing on an abandoned airfield in Guernsey and scouted the area. With this information, he made the statement that the islands were undefended. A platoon of Luftwaffe airmen was flown that evening to Guernsey airfield by Junkers transport planes. Inspector Sculpher of the Guernsey police went to the airport carrying a letter signed by the bailiff stating that "This Island has been declared an Open Island by His Majesty's Government of the United Kingdom. There are no armed forces of any description. The bearer has been instructed to hand this communication to you. He does not understand the German language." Jersey surrendered on 1 July. Alderney, where only a handful of islanders remained, was occupied on the second. A small detachment traveled from Guernsey to Sark, which surrendered on the fourth. Thus, the oldest held lands of the British nation, were lost without a single shot. The Germans quickly consolidated their positions. They brought in infantry, established communications and anti-aircraft defenses, established an air service with occupied mainland France, and rounded up British servicemen that were on leave in the islands.

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