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I have a Shuckle in Crystal, and it's holding a Berry. How long does it take for it to turn into Berry Juice, and how long does it take the Berry Juice to turn into Rare Candy?

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A Berry will only turn into Berry Juice for the first Shuckle with a Berry in the party and only if the player has reached Goldenrod City. Once the prerequisites have been met, there's a 1/16 chance after every battle.

Berry (Bulbapedia)
Pokegold (GitHub)

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It doesn't take too long, if you run up and down the route to goldenrod city it should be done.

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Does it work in B/W too?
No.....