Which Episodes Feature Sasuke Orochimaru Training With Orochimaru?

Man, this is one of those questions that made me go re-watch a chunk of the series with a mug of tea and way too many nostalgic feelings. Short version? Most of Sasuke’s proper training with Orochimaru actually happens off-screen during the time-skip between 'Naruto' and 'Naruto: Shippuden'. But if you want the on-screen moments where you actually see him with Orochimaru (or get close flashbacks that show what went down), there are a few places in both the original series and 'Naruto: Shippuden' to zero in on.

In the original 'Naruto' you’ll want to watch the episodes around the tail end of the ‘Sasuke Retrieval’ storyline and its immediate aftermath — that’s when Sasuke defects and first comes under Orochimaru’s influence. The anime shows the lead-up to his leaving Konoha, the initial encounters with Orochimaru, and the scene where Sasuke receives the Cursed Seal. Those episodes establish why Sasuke sought Orochimaru out and hint at what he wanted to learn. Even so, the detailed hour-by-hour grind of his training isn’t shown there because the series skips that period.

When you jump into 'Naruto: Shippuden', you start getting more flashbacks and scenes that reference or briefly show things from Sasuke’s training period. A handful of episodes highlight his relationship with Orochimaru, the experiments, and how that power affected him mentally and physically. Importantly, there’s also the arc where Sasuke goes back and confronts Orochimaru to put an end to him—those episodes show interaction, fighting, and the consequences of the training (and they’re well worth watching if you want to see how the student finally handles the teacher).

If you want the fullest picture beyond the main series, check out related extras: some OVAs and light novels constructed later dive into bits of Sasuke’s path and give more context to the off-screen months. Also, the manga fills in motivations cleanly if you’re comfortable switching mediums. Personally, I like watching the late-Part I sequences, then skipping to the Shippuden episodes that reintroduce Orochimaru and Sasuke’s later face-off: it gives a satisfying arc from ‘why he left’ to ‘what he learned’ to ‘what he ultimately did with that power’. If you're after specific moment-to-moment training scenes, they’re rare—most of the gritty practice, discipline, and development are implied off-screen—so mix the canon episodes with the flashbacks and extra material for the best feel. If you want, tell me whether you’re watching dub or sub and I can point to the more exact episodes that show the confrontations and flashbacks in your version — I’ve got a soft spot for tracking down those scenes.