Quote:
Originally Posted by Fat Minwu
How often do you "roll"? Every battle? Every turn?
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After every battle, as long as the pokemon that knows pickup is not holding an item, there is a 10% chance of that pokemon picking up an item. If the pokemon has picked up an item there is a 1% chance that that item will be the TM. I usually have 5 high level pickup pokemon while I'm training one pokemon for maximum item gain.
More details for pickup on the
bulbapedia page.