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I have a question about Cheap Shot. The Backstab move gives you several options, only one of which is to cause an extra +d6 damage.

Cheap Shot says "When using a precise or hand weapon, your backstab does an extra +1d6 damage."

My question is: does the extra damage from Cheap Shot only occur when the Thief chooses to do extra damage with Backstab? Or does it happen no matter what they choose?

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Only when you would deal damage with Backstab

As the wording says "extra" damage it would apply whenever you are already dealing some damage, whether that is the "free" damage option from Backstab or if you successfully rolled DEX and selected the damage dealing option from the list.

If you only selected the "Deal 1 damage to their armor" option, then there is no damage to apply "extra" damage to, so it would not apply.

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