After escaping from Imperial forces in the Hoth system, Han Solo brought his damaged Millennium Falcon to Cloud City for repairs. Lando, who once owned the Falcon until he lost it to Solo in a sabacc game, welcomed Solo and his companions to the facility, promising to get his techs right to work on the Falcon's troublesome hyperdrive. While he played the cordial and dashing host, Lando was setting Solo up for a fall - though the fall that came was not the one Lando had agreed to. He went along with Vader because the Dark Lord had claimed to be after someone named Skywalker. Solo, Leia, Chewbacca, and C-3PO were nothing more than bait, the Dark Lord had claimed, explaining that after the trap had been sprung, the four could remain on Bespin. The Empire's promise to leave Cloud City to its own devices and the large number of heavily armed stormtroopers at Vader's side had convinced Lando to go along with the deal. When he discovered that Vader was changing the terms to suit his own purposes and that his beloved Cloud City was about to become an armed camp, Lando finally decided to help Han. He ordered the evacuation of Cloud City, but was too late to rescue Han Solo from the bounty hunter Boba Fett. Instead, he helped Leia and Chewbacca escape in the Falcon, and even managed to help save Luke Skywalker from the very bottom of the floating city.

Later, Lando took part in the mission to rescue Han Solo from the clutches of Jabba the Hutt. His role in that mission was one of deceit, for he disguised himself as one of Jabba's guards and worked his way into Jabba's court so that he could watch, listen, and wait for an opportunity to make a move. After saving Solo and helping to destroy Jabba the Hutt, Lando decided to take a commission in the Rebel Alliance. Due to his reputation as a soldier-of-fortune, especially for his role in the Battle of Taanab, Lando was given the rank of general. He then volunteered to lead the starfighter assault on the second Death Star, a job that was made much easier by Solo's generous offer of the Millennium Falcon. At the helm of the Falcon, Lando's daring, expertise, and quick thinking were pivotal in the great space battle that took place above Endor's forest moon. In fact, he accompanied Wedge Antilles on the run to destroy the Death Star's power core. In the end, Lando was decorated as a hero alongside Luke Skywalker, Han Solo, and Princess Leia.