PokéBase - Pokémon Q&A
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I haven't used Rest on a Pokemon since like Generation II so the mechanics of the game may have changed, but from what I remember, even if your Pokemon switches out, if the battle ends, etc. the counter for Rest usually remains. However, I am playing Pokemon Y right now, and had my Ferrothorn use rest on a wild Pokemon, waited a turn, and then ran. On the next encounter of a Pokemon, it was asleep for another two full turns before running, and then on the last encounter of a Pokemon, it didn't wake up until the third turn. Why is this?

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A sleeping Pokemon will wake up in at least 5 turns this counts for rest since you ran away from (pokemon 1) that got rod of the turns so the next battle will need at least 5 turns to wake up hope I helped :)

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In which generation did the counter start resetting for rest? It used to remain even after switching out or ending the battle......
it does still stay if you run or switch out this just causes the pokemon to reset except for status conditions (on your case sleep)