Lt. Paul Pentland joined the 2nd Battalion, 48th Highlanders in Toronto and is shown in a 1940 newspaper article as one of the 52 officers of the 2nd Battalion who were training for service in the Second World War. Once in England he joined the 1st Battalion, 48th Highlanders. When the battalion sailed for Sicily in  June 1943 Lt Pentland remained behind as a replacement officer for casualties or transfers incurred by the battalion in Sicily and Italy. He rejoined the 1st Battalion in Italy and was in the May 17, 1943  advance up the Liri Valley to Pontecorvo and the Hitler line he was noted for showing aggressive leadership leading his Platoon in Baker Company. He was wounded during the Gothic and Rimini Line battles in September and after hospital rejoined the battalion while they were at rest south of Santarcangelo, Lombardy in mid October.