Tobruk's sortie during Operation Crusader in November 1941

The sortie by Tobruk's garrison during Operation Crusader began early on 21 November 1941. The Polish brigade's attack followed the plan. They got the enemy's attention, although did not mislead anyone. They drew enemy fire, but not an extreme amount. The 23rd Brigade attack also followed the plan, but was not able to capture the outpost Plonk. They did create a stir and attract the enemy's attention.
The force from Tobruk was able to form-up successfully. The enemy did not interfere with the operation. The artillery firing and the demonstration by the 23rd Brigade created enough noise that the enemy was not able to hear the noise from the vehicles driving into position. The enemy had responded to the 23rd Brigade activities with counter-battery fire that helped to mask vehicle noise. The infantry would set off at about 6:30am. To the left, the enemy had occupied outpost Butch, so Butch would need to be "neutralized". For the sortieing force would pass Butch on the way to the Tiger outpost. The 2/King's Own was ordered to take Butch. The 2/Black Watch would attack Tiger after overrunning outpost Jill. On the left, the 2/Queen's would attack Tugun. This was "far on the left flank".
Artillery started firing at outpost Butch at 6:20am. The 2/King's Own only took ten minutes to capture outpost Butch. They were supported by nineteen Matilda tanks from the 7th RTR. They killed 30 Germans at Butch and took ten prisoners. The British had expected that Butch would be near the boundary between two Italian divisions and would be backed by a few "strong points". In fact, the area was a defended position held by German infantry. They had apparently only moved into the area about six days before being attacked. The captors found documents describing a system of defensive positions with code names that were concealed. There were minefields that had no markings. There were enemy positions north of Butch which were not attacked for a number of days.
The Black Watch attackers moved forward at 6:30am. They were to take heavy casualties, as they lost half of their men. They were not accompanied by any tanks. The only tanks nearby were a "squadron of cruisers" which were being saved for later. They found that they took longer to pass over the bridges across the anti-tank ditch. The infantry commanders had decided to conduct their assault without tanks, as they wanted to take advantage of the artillery supporting fire that would be fired on a timed schedule.
The attack did not go as planned, although brave soldiers led by good men did the best that could be done. The plan assumed that Jill could be easily overrun, but Jill was actually strongly held. The men of the Black Watch tried to move forward, but were shot. The Matilda tanks and a company of the 2/King's Own eventually arrived and that allowed them to overrun outpost Jill. The Black Watch had lost a company in the process of attacking Jill. That left them without the force needed to attack outpost Tiger. This is based on the account in Vol.III of the Australian Official History.