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The Anastasia was a Union-class DropShip commanded by Weltallhauptmann Alvin Lippard, operated by Skye separatists in the Second Skye Rebellion where it took part in General-Kommandant Friedrich Wilhelm von Bulow's attack on Glengarry. The fleet jumped from Skye to the Glengarry system on 1 April 3056.
With the defenders outmatched by the attacking forces, Glengarry's Governor General DeVries sought to effectively surrender to spare his planet the destruction he felt would be inevitable otherwise. DeVries thus negotiated a secret deal with von Bulow and attempted to sideline the planetary garrison (elements of the Gray Death Legion). However, his plot was uncovered while von Bulow's DropShips were still approaching the planet and the defenders used the arrangement, and DeVries's daughter Caitliln DeVries (who was a Gray Death Legion cadet) to lure the vanguard of the attack into a trap.
Von Bulow was cautious enough to send only two DropShips ahead to land on the spaceport of the capital city of Dunkeld, the Anastasia and the Leopard-class Raven. They were promptly ambushed by the weaker defenders in an intricate battle plan that allowed the defenders to evacuate their own DropShip Europa to escape and hide in the mountains while luring the ground forces into a trap by blowing up the DropShip Medea around them. The Raven and the Anastasia escaped the debacle with some damage. The altogether sixteen BattleMechs under Oberst Wilhelm Streiger that they had deployed were lost, as were at least some (possibly all) of their aerospace fighters.
Von Bulow subsequently ordered Weltallhauptmann Lippard executed for having withdrawn from the battle too early, and ordered the Anastasia be placed under the command of Lippard's XO. It is unclear if these orders were carried out.
On 11 April the empty Anastasia and Raven, still carrying the marks of the Dunkeld battle, assisted the DropShip Katerina in the landing at Loch Sheol which, however, was just a decoy operation; the DropShips were recalled quickly.
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