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In S4E1, we see Twilight Sparkle flying fast with Spike on her back. Heading directly towards the Golden Oak Library, she's going too fast to stop, so she teleports herself inside. Spike remains, keeping his momentum and crashing into the window (he was alright).

In S4E4, we see Twilight Sparkle with a ring, trying to keep it away from a bunch of badguysponies. She teleports away from them, taking the ring with her.

So my question is, when teleporting, what can she take with her, and what not?

Are there actual rules to that, or is it just as the plot demands / deems funny?

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In S2 E21 “Dragon Quest”, Twilight teleports herself together with two other ponies, Spike, and a dragon egg. Thus, even at that point Twilight could take three other creatures with her. I think that's quite impressive. I guess in S4 E1, Twilight either just wasn't thinking fast enough and forgot to take Spike with her, or else she thought it might be dangerous to take Spike.

As another example, in S4 E21 “Testing testing 1, 2, 3” Twilight teleports herself and Rainbow Dash. Also, in MLP: Equestria Girls, Sunset Shimmer teleports together with her saddlebag, which shows definitely that ponies can carry equipment when they teleport (not that I'd ever doubt that).

Further, we have seen Twilight teleport others without moving herself: in S2 E10 “Secret of my Excess” she teleports Spike.

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    Also notable is S01E03 "The Ticket Master", in which Twilight teleports herself and Spike from some location in Ponyville to inside the library, and Spike ends up burnt. – jwodder Nov 15 '14 at 18:17

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