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The assault went in under the cover of darkness on the morning of 21 January. Once it appeared that the 2nd/3rd Battalion had penetrated the Italian forward defences, the leading companies of the 2nd/1st Battalion started their advance. However, one of the Australian companies soon ran into booby-traps that killed or wounded several in a platoon. Major Abbot's company was given the task of clearing several bunkered platoon, which it took after some fierce fighting, having initially been held up by the defenders manning Post 55. Sergeant Hoddinot had to crawl forward and use hand grenades to overcome the bunkered platoon that had wounded his platoon commander (Lieutenant MacDonald and a section commander (Corporal Foster) in his platoon. For his courage and leadership in the action, Hoddinot won the Distinguished Conduct Medal (D.C.M) and was later promoted to captain.

The assault went in under the cover of darkness on the morning of 21 January. Once it appeared that the 2nd/3rd Battalion had penetrated the Italian forward defences, the leading companies of the 2nd/1st Battalion started their advance. However, one of the Australian companies soon ran into booby-traps that killed or wounded several in a platoon. Major Abbot's company was given the task of clearing several bunkered platoon, which it took after some fierce fighting, having initially been held up by the defenders manning Post 55. Sergeant Hoddinot had to crawl forward and use hand grenades to overcome the bunkered platoon that had wounded his platoon commander (Lieutenant MacDonald and a section commander (Corporal Foster) in his platoon. For his courage and leadership in the action, Hoddinot won the Distinguished Conduct Medal (D.C.M) and was later promoted to captain.

An Italian platoon also fought well in defence of Post 62, despite British tank and artillery fire. Lieutenant Clark had to pour a mixture of crude oil and kerosene through the firing slit in order to silence the bunkered defenders. Eleven Italians were killed and the remaining 35 surrendered. As Captain Campbell's company reached the end of the first phase of the advance it came under fire from dug-in light tanks. Captain Anderson and Lieutenant Russell were wounded and Lieutenant Russell killed. Despite encountering some stiff opposition, the 2nd/8th Battalion took 1,300 prisoners. At the same time, Italian gunners brought down fire on the battalion and in the early afteroon infantry counterattacked with the support of a tank squadron.

An Italian platoon also fought well in defence of Post 62, despite British tank and artillery fire. Lieutenant Clark had to pour a mixture of crude oil and kerosene through the firing slit in order to silence the bunkered defenders. Eleven Italians were killed and the remaining 35 surrendered. As Captain Campbell's company reached the end of the first phase of the advance it came under fire from dug-in light tanks. Captain Anderson and Lieutenant Russell were wounded and Lieutenant Russell killed. Despite encountering some stiff opposition, the 2nd/8th Battalion took 1,300 prisoners.

Under pressure from this strong battalion force, Campbell's company had no option to withdraw, having lost 100 killed, wounded and captured. At this point help arrived in the form of two British Matilda tanks. The Australian rifle companies fought back with grenade, Bren, rifle and bayonet. They were met by a hail of fire on various occasions. Lieutenant Trevorrow and Sergeant Duncan were seriously wounded, and two of the platoon commanders had bullet holes in their clothing or equipment. At this point Captain McDonald called forward two of the British Infantry tanks to engage another stubborn platoon defending Post 42. After some fierce close-quarter combat the Italians relinquished Post 41. As Captain Abbot's company renewed the advance it came under effective fire from the Italian platoons dug in in and around Posts 34 and 35, and was forced to withdraw.

At around 14:00 hours, the Italians mounted a determined battalion-sized infantry-armour counterattack and Campbell's company had no option to withdraw, losing many killed, wounded or captured, before help arrived in the form of British anti-tank guns and tanks. At this point help arrived in the form of two British Matilda tanks.<ref>"The advance was resumed at 14:00 and once again the 2/8th Battalion bore the brunt of the action, almost immediately running into an Italian counter-attack involving  several hundred infantry supported by a dozen M13/40 tanks, seven of which got in amongst the Batalion's left hand company and overran its leading platoon ... The situation was saved by two Australian sergeants manhandling a captured Italian anti-tank gun into action and the arrival of two 2-ponder Portees from the 3rd RHA." (Tobruk: The Great Siege, 1941-42, William F Buckingham, The History Press, 2012)</ref>Meanwhile, other Australian rifle companies made good progress, using grenade, Bren, rifle and bayonet. They were met by a hail of fire on several occasions. Lieutenant Trevorrow and Sergeant Duncan were seriously wounded, and two of the platoon commanders had bullet holes in their clothing or equipment in the close-quarter fighting. At one point, Captain McDonald had to request the help of

two British tanks to silence another stubborn platoon defending Post 42. After some fierce close-quarter combat the Italians gave up Post 41. As Captain Abbot's company also came under effective fire from the Italian platoons dug in in and around Posts 34 and 35, and was forced to withdraw.

During the night, the 19th Brigade commander attempted to negotiate a ceasefire with the commander of the Italian garrison in Tobruk. It was hoped they would succeed, but a cable from the Italian Supreme Command put paid to their efforts. Mussolini himself had himself personally signaled to General Petassi Manella, forbidding him to surrender and informing him that formations of Italian bombers were on their way as reinforcements. Later that night Italian SM.79s carried out a surprise low-level attack, but bombed some 8,000 prisoners who had been gathered inside a fenced enclosure, killing and wounding hundreds of their men. This bombing helped break the will of among those determined to fight it out in the town.

During the night, the 19th Brigade commander attempted to negotiate a ceasefire with the commander of the Italian garrison in Tobruk. It was hoped they would succeed, but a cable from the Italian Supreme Command put paid to their efforts. Mussolini himself had himself personally signaled to General Petassi Manella, forbidding him to surrender and informing him that formations of Italian bombers were on their way as reinforcements. Later that night Italian SM.79s carried out a surprise low-level attack, but bombed some 8,000 prisoners who had been gathered inside a fenced enclosure, killing and wounding hundreds of their men. This bombing helped break the will of among those determined to fight it out in the town.