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Background Pony #C3D2
How is it over-thinking? I agree with #2E4F, I always had a problem with that nonsensical dream KGB deus ex machina power, because either everything was fine through 1000 year imprisonment, or pony dreams are filled with horrors trying to murder ponies like three dream walking episodes suggested feebly trying to justify Luna spying on everyone — which would ironically mean Celestia did massive "what the hell hero" by imprisoning Luna instead of trying to cure her killing countless thousands bereft of dream guardian through that millennium. You can't have it any other way, either Luna is necessary or she is worse monster than KGB or Stasi ever were, because they at least didn't dabble in mind reading and dream altering…
Background Pony #8B07
Celestia: Enters Luna's part time job as the Dream Watcher. "Oh, so this is what my sister does besides raise the moon. Wow, so many dreams. Okay, Celestia. You can do this. Piece of cake."

Celestia: "Hmmm, I wonder what Derpy's dreaming of right now?"

Celestia: Sees Derpy's dream in front of her just now. "…Sigh. Really, Derpy?"

Celestia: "Note to self, send Derpy to the moon later when I get back for dethroning me in her dreams."
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Lord of the Empty Seat
@Background Pony #2E4F
Not really, as shown in the three CMC episode she appeared in, she can actually sense this kind of thing. Therefore avoiding any mistakes.

I don't know how they handled the Thousand-Year thing, then again they never explain how Celestia could just take over her sisters role as moonraiser either.
Background Pony #9DCD
How does she know if a dream is a nightmare or pleaseant dream?

What if someone has an erotic fetish dream that turn into a nightmare?

It doesn't make sense. Dreams are natural part of psyche along with nightmares. Pony dreams act the way like our work and they don't leave any negative marks. Even the ponies in the show had no dream walking guardian for last 1000 years. That entire plotline was pointless and just to make Luna look cool as some living animated dream catcher.
Background Pony #9DCD
Its a main reason why Lunas job is completely useless and hurtfull.
Most of the ponies don't want the Princesses to see their erotic wet dreams. Never understood why theur invent the dream walking ability for Luna. Seem like a massive derp of the show writers. Them may as well establish that Celestia spy on every citizien of Equestria with a all seeing eye.
Background Pony #8658
I will never be able to figure out which of these dreams I like best. I mean they're all pretty good, but how can you choose between DJ Flurry and what appears to be a Red Dwarf/Pinkie Pie crossover moment?
Background Pony #9DCD
I think Discord would dream of Fluttershy while Smooze would just want to play silly games so i'm guessing it's Smooze.
Background Pony #7A38
that Celestia's reaction toward Derpy's dream;

I hope she didn't end up being send to the moon after this.