Lt. Blair Eby 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. Travelling to England to the Holding Unit he was promptly sent to the 1st Battalion, 48th Highlanders of Canada in England in January 1943. For the sailing to Sicily in June 43 Lt Eby was a platoon commander in Charlie Company. Following the Sicilian campaign and advance up the Adriatic side of Italy, Lt. Eby was awarded the Military Cross for his skillful and hands on leadership near San Marco (see MC Commendation). Shortly after he suffered from jaundice, contracted in Sicily, and returned to the battalion at Torella in the last week of November. In February, Captain Eby was transferred to a post at brigade HQ, and in July 1942 transferred to a staff post with 12th Infantry Brigade.