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Boers besiege Ladysmith, Mafeking and Kimberley

The Boers struck first on 12 October at the Battle of Kraaipan, an attack that heralded the invasion of the Cape Colony and Natal between October 1899 and January 1900. With speed and surprise, the Boers drove quickly towards the British garrison at Ladysmith and the smaller ones at Mafeking and Kimberley. The quick Boer mobilisation resulted in early military successes against scattered British forces. Sir George Stuart White, commanding the British division at Ladysmith, unwisely allowed Major-General Penn Symons to throw a brigade forward to the coal-mining town of Dundee (also reported as Glencoe), which was surrounded by hills. This became the site of the first major clash of the war, the Battle of Talana Hill. Boer guns began shelling the British camp from the summit of Talana Hill at dawn on 20 October. Penn Symons immediately counter-attacked: His infantry drove the Boers from the hill, for the loss of 446 British casualties, including Penn Symons.

Another Boer force occupied Elandslaagte, which lay between Ladysmith and Dundee. The British under Major General John French and Colonel Ian Hamilton attacked to clear the line of communications to Dundee. The resulting Battle of Elandslaagte was a clear-cut British tactical victory, but Sir George White feared that more Boers were about to attack his main position and so ordered a chaotic retreat from Elandslaagte, throwing away any advantage gained. The detachment from Dundee was compelled to make an exhausting cross-country retreat to rejoin White's main force. As Boers surrounded Ladysmith and opened fire on the town with siege guns, White ordered a major sortie against their positions. The result was a disaster, with 140 men killed and over 1,000 captured. The siege of Ladysmith began: it was to last several months.

Meanwhile, to the north-west at Mafeking, on the border with Transvaal, Colonel Robert Baden-Powell had raised two regiments of local forces amounting to about 1,200 men in order to attack and create diversions if things went amiss further south. As a railway junction, Mafeking provided good supply facilities and was the obvious place for Baden-Powell to fortify in readiness for such attacks. However, instead of being the aggressor, Baden-Powell was forced to defend Mafeking when 6,000 Boer, commanded by Piet Cronjé, attempted a determined assault on the town. This quickly subsided into a desultory affair, with the Boers prepared to starve the stronghold into submission. So, on 13 October, the 217-day siege of Mafeking began.

Lastly, over 360 kilometres (220 mi) to the south of Mafeking lay the diamond mining city of Kimberley, which was also subjected to a siege. Although not militarily significant, it nonetheless represented an enclave of British imperialism on the borders of the Orange Free State and was hence an important Boer objective. In early November, about 7,500 Boer began their siege, again content to starve the town into submission. Despite Boer shelling, the 40,000 inhabitants, of which only 5,000 were armed, were under little threat, because the town was well-stocked with provisions. The garrison was commanded by Lieutenant Colonel Robert Kekewich, although Rhodes was also a prominent figure in the town's defences.

Siege life took its toll on both the defending soldiers and the civilians in the cities of Mafeking, Ladysmith, and Kimberley as food began to grow scarce after a few weeks. In Mafeking, Sol Plaatje wrote, "I saw horseflesh for the first time being treated as a human foodstuff." The cities under siege also dealt with constant artillery bombardment, making the streets a dangerous place. Near the end of the siege of Kimberley, it was expected that the Boers would intensify their bombardment, so Rhodes displayed a notice encouraging people to go down into shafts of the Kimberley Mine for protection. The townspeople panicked, and people surged into the mineshafts constantly for a 12-hour period. Although the bombardment never came, this did nothing to diminish the anxious civilians' distress. The most well-heeled of the townspeople, including Cecil Rhodes, sheltered in the Sanatorium, site of the present-day McGregor Museum; the poorer residents, notably the black population, did not have any shelter from shelling.

In retrospect, the Boers' decision to commit themselves to sieges (Sitzkrieg) was a mistake and one of the best illustrations of their lack of strategic vision. Historically, it had little in its favour. Of the seven sieges in the First Boer War, the Boers had prevailed in none. More importantly, it handed the initiative back to the British and allowed them time to recover, which they did. Generally speaking, throughout the campaign, the Boers were too defensive and passive, wasting the opportunities they had for victory. Yet that passivity also testified to the fact that they had no desire to conquer British territory, but only to preserve their ability to rule in their own territory.