The First Time Darth Vader Failed Palpatine & How He Was Punished [Legends]

We all know Vader as the unstoppable enforcer of the Empire, the man who hunted Jedi and crushed rebels without mercy. But in the early days of his service to Palpatine, Vader wasn’t perfect. In fact, there was one mission—his first real failure—that ended with Vader humiliated, alone, and forced to reflect on how easily he’d been tricked. And yes, Palpatine made sure that lesson was painful.

Vader’s Obsession With Hunting Jedi

After Order 66, Vader wasn’t content with just watching the Jedi fall, he wanted to finish the job himself. But his obsession with personally hunting down survivors wasn’t exactly what Palpatine had in mind. In Purge – The Hidden Blade, we see just how far Vader was willing to go, and how badly it ended for him.

Palpatine gave Vader a simple task: guard a secret AT-AT factory on a remote world and keep production running. That’s it. Don’t chase Jedi, don’t waste time—just protect the factory.

But when the factory was repeatedly attacked by the planet’s native resistance fighters, Vader couldn’t help himself. He suspected a Jedi was behind the attacks and sent out a scouting team to confirm it. When that team vanished, he reported back to Palpatine—and got immediately scolded for focusing on the wrong thing again.

Vader Realizes the Jedi Outsmarted Him

Soon after, one scout returned, barely alive. Before dying, he confirmed what Vader had suspected: the leader of the natives was a Jedi. That was all it took.

Ignoring Imperial orders and Palpatine’s direct instructions, Vader went off alone into the wilds to hunt down the Jedi. He cut through the camp and confronted the first target, a Padawan. Vader executed him without hesitation.

But the real enemy, the Jedi Master, was still out there. As Vader pressed deeper into the forest, the natives ambushed him again, this time using a sonic device that awakened a massive beast. Realizing his lightsaber was useless against its thick hide, Vader reached out with the dark side and dominated the creature’s mind, turning it into his personal mount.

It was a clever move — but one that would ultimately seal his failure.

Vader finally found the Jedi Master sitting calmly atop a mountain, waiting. The Jedi wasn’t running. He had no intention of hiding. This was a trap—and Vader had walked right into it.

They fought. Vader disarmed him and was about to strike the final blow. But the Jedi pulled out a second hidden blade and briefly turned the tables. Vader recovered quickly, using the Padawan’s stolen saber to finish him off.

Before dying, the Jedi revealed his name — a word that, in his native tongue, meant “trickster.” It wasn’t just a name. It was the lesson.

Vader returned to the factory… or what was left of it. The entire facility had been reduced to rubble. The same sonic device used to wake the beast had been placed there too. The creature Vader had controlled had returned and destroyed everything in his absence.

That’s when Palpatine arrived.

He didn’t need to say much. The look of disgust on his face said it all. His apprentice had ignored orders, abandoned his post, and let his obsession cause a total failure. Palpatine simply told him to “meditate on his failure” and left him behind on the ruined planet.

That was his punishment—abandonment, isolation, and shame.