He gained fame by his actions in sinking a German vessel with a milk can while serving as a POW stevedore in Tobruk harbour, for which he was awarded the Military Medal.

[1] Maseko became a prisoner of war on 21 June 1942 when Major-General Hendrik Klopper, commander of the South African 2nd Infantry Division surrendered the Tobruk Garrison with 32,000 men to Field Marshal Erwin Rommel.

Using ammunition from which he extracted the cordite and a long fuse, Maseko put together an improvised explosive device which he stashed among jerry-cans of gasoline in the ship's hold.

[3][6] The next day, the POWs were questioned about smoking while on board ship – to which they answered that cigarettes were forbidden and were not included in any rations, which could not be disputed by their Italian captors.

[5] Maseko later escaped from the Italian POW camp in Tobruk and walked for three weeks through the desert and enemy lines to El Alamein.

[7][6] In October 1942 he joined in the defeat of his German and Italian captors as a stretcher bearer with the 1st South African Infantry Division in the Second Battle of El Alamein.

[8] After El Alamein, he was transferred to the 6th South African Armoured Division and was gazetted as a recipient of the Military Medal (MM) for his actions in Tobruk on 11 March 1943.

For meritorious and courageous action in that on or about the 21st July, while a Prisoner of War, he, Job Masego, sank a fully laden enemy steamer - probably an "F" boat - while moored in Tobruk Harbour.

In carrying out this deliberately planned action, Job Masego displayed ingenuity, determination and complete disregard of personal safety from punishment by the enemy or from the ensuing explosion which set the vessel alight.