Major Jack Pritchard, Royal Tank Regiment, was most likely captured in North Africa in 1942, even though there is no precise indication as to where or when exactly. It is certain, instead, that he was in PG 29 Veano on 9 September 1943, when the Armistice between Italy and the Allies was proclaimed.

The following day, «[the PG] was taken over by the P/W without Italian resistance», and the day after, the Senior British Officers allowed the PoWs to leave the camp. Pritchard left Veano with Major Fryle, Major Cole and Private Kemsley, all of whom were former members of his tank battalion.

The four escapees remained in the Bettola area until the end of October 1943, when the increased frequency of Fascist raids, coupled with the worsening weather conditions, forced them to move. Local families once again aided them, particularly the one who had fed them near Veano. The Italians, in fact, suggest to the escapees to go to Milan and live there. Cole, Frye and Pritchard went to the city and were sheltered there (Cole and Frye with the family who brought them to Milan, Pritchard with a different one). However, perhaps because of the more frequent activity of the Fascists and the Germans, the Italians refused to repeat the journey to bring Kemsley «or other parties whom we had hoped to help». 

The three decided to stay in Milan, hoping that the Allies would continue their offensive and liberate the city quickly.

In December, Cole and Frye met an Italian from Monza. «He was very pro-British and insisted on helping us and our two Italian families with money». However, Pritchard noticed that all their helpers were incredibly tense. Their hosts, for example, «would not tell even their closest friends of our existence, and were not very willing to let us out of their houses, owing to the danger of people seeing us». Only at the end of the month were the escapees allowed to leave their safe houses. Pritchard and his companions, however, were not concerned only with taking a breath of fresh air: «our object was to find contacts and to know our way about MILAN».

During the following period, Pritchard was involved in two failed attempts to leave Italy. The first one, in February, involved their relocation to the Adriatic coast to wait for an Allied boat to rescue them. The second one also involved a boat, this time leaving from Genoa. Both these attempts, however, never took place.

In May 1944, the three escapees met an Italian «who appeared to be in contact with Allied Intelligence». The mysterious man probably belonged to the Franchi organisation (guided by Edgardo Sogno; it was a liaison organisation between the Allies and many partisan formations), maybe even Sogno himself. «We offered to help him, but he refused this and told us that he thought the best for us would be to go to SWITZERLAND». Pritchard and his companions, now convinced that the Italian campaign would last quite a while, decided to accept this offer. However, just a small oversight was enough to put everything in jeopardy:

Pritchard moved to the city’s outskirts and met with the local partisans, most likely a group of GAP or SAP. «In Jul[y] 44, when I was staying in a house in the suburbs of MILAN with five Partisans on my way to join their band, we were surprised by the Fascists. After a short battle, we escaped, but I lost contact with the Partisans».

Pritchard continued to live in Milan, often changing his residence and host. He was always aided by the Italians who protected him from the start, including the former protectors of Cole and Frye. The chance to leave the country presented itself to Pritchard only in September 1944, when he met some Italians who were part of an organisation whose aim was to save and rescue Allied PoWs (it is unclear whether this group was formed by individuals he had never met, or if it was again the Franchi organisation). These men finally brought him to the Swiss border on 26 October 1944. Pritchard had spent more than a year on the run, most of this time not in the countryside, like many other escaped PoWs, but in Milan, one of Italy’s largest cities, in the heartland of the Social Republic.