Following the British victory at Elandslaagte General White ordered all the British forces to fall back on Ladysmith. The Transvaal Boers followed up and soon occupied the high ground dominating the town. When news arrived that the Orange Free State Boers were on the way to join the Transvaal Boers, White decided to attack the enemy positions to prevent a junction of their forces.
White, having previously served in India, had no experience of facing troops armed with modern weapons and underestimated the abilities of the Boers to manoeuvre as well as to fight. He attempted a double envelopment of the Boers with Carleton advancing on the left and Grimwood on the right whilst Colonel Hamilton (with the Brigade that had been engaged at Elandslaagte) attacked Pepworth Hill in the centre.
On the morning of 30 October, with the attacks on either flank having failed, Colonel Hamilton found himself required to make a frontal attack on the central Boer position on Pepworth Hill. The Boers had a strong gun line established on the Hill which included a Long Tom gun that could out-range the British artillery and reach to Ladysmith itself.