As a general rule, if an item adds some effect or bonus to your attack, you must decide to use it before attack modifier cards are drawn.
Equipped items are active from the beginning of the scenario, such that if an item reacts to an enemies actions, it can do so immediately.
Item cards with circles to track multiple uses act exactly like persistent ability cards, in that if the situation applies, you must use the item in reaction and lose a charge. Additionally, it should be noted that if the card has a spent icon in the lower right corner, it is not technically spent until all charges have been lost, and so cannot be refreshed through resting or other abilities until all charges have been used.
If an item card does not have circles to track multiple uses, then you can decide when to use it - it is not mandatory.
If an item says "Heal X damage," this is functionally equivalent to "Heal X, Self." It interacts with wound and poison like any other heal ability.
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