An attempt to capture Baron Administrator Lando Calrissian was orchestrated by the bounty hunter Bossk in 1 ABY. Calrissian had previously acquired Cloud City from Dominic Raynor through a victory in a sabacc game. Raynor, convinced that Calrissian had cheated, contracted Bossk to exact retribution on the gambler. Recognizing the futility of a direct confrontation, the bounty hunter devised a scheme to ensnare the new Administrator. Bossk assembled a mercenary squad and infiltrated the lower levels of the city, where they sabotaged equipment on a maintenance level, intending to lure Calrissian. Despite Calrissian's caution in bringing several troopers, he fell into the trap and was isolated from communication when a blast door sealed behind him. Calrissian managed to escape through a nearby hangar, and this assassination attempt did not prevent him from continuing to manage Cloud City.
Back in 1 ABY, within the Trest casino of Cloud City, which was a tibanna gas mining colony located in the atmosphere of the gas giant Bespin, Lando Calrissian, a known professional gambler, engaged in a game of sabacc. His gameplay attracted the attention of Baron Administrator Dominic Raynor, who then invited Calrissian to a game held in the Ecclessis Figg Room. During this high-stakes game, Calrissian ended up losing all of his cash, including his personal Mu-class shuttle, named the Cobra. However, after the game, Lobot, the cyborg computer liaison officer of the city, revealed that the game was in fact rigged by the dealer.
Despite the revelation, the loss was still considered legitimate for Calrissian. He and Raynor then engaged in another game, where Lobot provided Calrissian with a gift of five million credits from the city's workers. This time, Lobot, aided by Raynor's consort Ymile, who disliked living in the city, manipulated the game to favor Calrissian. The gambler then risked all five million credits and his remaining starships against Raynor's two million credits and Cloud City itself, which Calrissian ultimately won. The former Baron Administrator became convinced that the scoundrel had cheated and vowed to reclaim his losses. Utilizing his connections, Raynor hired the Trandoshan bounty hunter Bossk to pursue Calrissian and exact his revenge.
Aware that his target, the new Baron Administrator, would have protection, Bossk enlisted a group of mercenaries and dangerous individuals. This group included a Twi'lek scoundrel, another scoundrel of the same species, a Quarren assassin, and a Duros mercenary, all to assist him in dealing with any potential issues. After successfully bypassing Cloud City's security, Bossk sabotaged essential equipment to prepare for the ambush in one of the city's maintenance areas. Uncertain about which turbolift Calrissian would use, the Trandoshan divided his team, positioning them in rooms near all the lifts. Bossk instructed his team to take cover but remain visible to lure Calrissian. Their plan was to quickly kill any guards accompanying the Administrator and capture Calrissian before he could escape.
Once the hunters were in position, Bossk accessed the city's computer system and, posing as the chief engineer, sent an urgent message to Calrissian. The Trandoshan claimed that a vital repulsorlift pod was on the verge of failing, which threatened to send the entire city plummeting through Bespin's clouds. Calrissian responded immediately, bringing with him four Bespin Wing Guards and a female Twi'lek bodyguard.
As Calrissian and his guards entered the maintenance level, a blast door suddenly sealed behind them. Trapped in a dark, steamy room, they were immediately met with blasterfire from Bossk's bounty hunter team. The interference from the repulsorlift machinery prevented Calrissian from using his wrist link to call for reinforcements. Additionally, the maintenance deck's communication stations were inoperable due to Bossk's sabotage. Realizing that another access port was nearby, Calrissian understood that his only option was to fight and attempt to escape through the adjacent hangar.
Meanwhile, four loyal wing guards, alerted by the sounds of the firefight, were en route to assist the Baron Administrator. A member of Calrissian's group managed to reach the nearby flight control center and send a distress signal to Security Headquarters. The arrival of the four additional wing guards aided Calrissian in escaping through the nearby hangar bay.
Following the failure of Bossk's ambush, Raynor hired other individuals to assassinate Calrissian, but each attempt led to increased security measures for the Baron Administrator. After a Gank assassin also failed, Raynor dispatched a Human replica droid disguised as Queen Sarna of Drogheda, one of Calrissian's former lovers, to kill the gambler. The droid was directed to the Administrator's private office, but this assassination attempt also failed.
After this failed attempt, Calrissian conceived a plan to draw out his adversary by feigning his own death. Calrissian assumed that upon hearing news of his "death," Raynor would come to Cloud City to purchase the floating colony. In the meantime, Calrissian and Lobot traveled aboard the Cobra to the Yucrales sector in the Mid Rim to remain hidden. However, they were ambushed there by the female bounty hunter Thune and her modified YT-1300 light freighter, the Faceted. They managed to escape to Quilken, and with the assistance of Mungo Baobab—heir to the Baobab Merchant Fleet—they captured Thune. Calrissian and Baobab then used Thune as leverage to capture Raynor, who was interrogated by Bwahl the Hutt until he abandoned his vendetta.
The Cloud City ambush was featured in Sore Loser's Revenge, a Wizards.com online scenario for the Star Wars Miniatures collectible tabletop strategy game. Eric Cagle authored the scenario for Wizards of the Coast, and it was published online on October 8, 2004. The scenario suggested using the Tractor Beam Reactor Coupling map for gameplay. In an alternate ending to the scenario, Bossk captures Calrissian; however, the short story Lando Calrissian: Idiot's Array has rendered this ending non-canon by depicting Calrissian unharmed just days after Bossk's ambush.