On 29 June 1940, Kibby enlisted in the all-volunteer Second Australian Imperial Force, which had been raised for overseas service in World WarII. He was posted to the 2/48th Infantry Battalion, part of the 26th Brigade. This brigade was initially assigned to the 7th Division. On 14 September, when the battalion was training in South Australia, Kibby was promoted to acting corporal, and this was followed by promotion to acting sergeant a month later. The 2/48th embarked on the troopship HMT "Stratheden" on 17 November and sailed for the Middle East, where it disembarked in Palestine on 17 December. On New Year's Eve, Kibby fell into a slit trench and broke his leg. He then spent months convalescing. During his recovery, he produced at least forty watercolours and pencil drawings, which, according to his biographer, Bill Gammage, displayed "a fondness for Palestine's countryside and a feeling for its people". While in Palestine, Kibby struck up a friendship with the painter Esmond George, and occasionally accompanied him on sketching trips. After recovering, Kibby joined the brigade training battalion in August 1941 and also attended the infantry school to complete a weapons course. He rejoined the 2/48th in February 1942, the 26th Brigade having been transferred to the 9th Division a year earlier. At the time, the battalion was undertaking garrison duties in northern Syria, after participating in the siege of Tobruk.