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If my Gardevoir (with Synchronize) uses Rest, will the opposing Pokemon fall asleep?

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NO
> Synchronize will not pass on the Sleep or Frozen status conditions, or if the status condition was obtained from items such as the Flame Orb.

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No.
>If the opponent causes a burn, paralysis, or poisoning of a Pokemon with Synchronize, the opponent receives the status condition too. Self-inflicted status conditions (for example through the use of an item) are not passed on.

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