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Say I upgrade a character that already has a Bounty ability with Valuable Contract. If it does enough attack damage to an enemy to KO it, what happens?

In that case, you’ll get to use both Bounty abilities in either order. You can’t use the character’s Bounty ability twice or Valuable Contract’s Bounty ability twice though.
Source: Wizards of the Coast (2019-11-08)    【Link to Ruling】
Tags: Valuable Contract