Rules FAQ
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Reactions to a card being pillaged come later than reactions to winning the challenge (and later than reactions to claim being applied). If you draw something like We Do Not Sow with Asha's ability, the window to play it during that challenge has already passed.
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If you have multiple characters with pillage in the same challenge, you choose their order (this matters for cards like Silence's Crew (TRW)), but all the cards are still pillaged simultaneously. The reaction window opens after all the cards have been pillaged, so the value of X should be the same wherever Asha is in the order (but may change if you trigger reactions like Nute the Barber before hers). If Harren the Black is in play, additional cards will also be discarded for each pillaged card before Asha's reaction can be triggered.
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If you trigger Scouting Vessel, Asha is considered to have pillaged 3 separate cards. However, you can still only trigger the reaction once due to her once per phase limit. Note that the limit is new in this version of the card compared to the original one. The other difference is that you have to reveal the card you search for now.