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When I take the level 3 Herbal Poultice Item, how does it work? It's a potion which does the following:

Use before you or an ally takes a short rest. The target of the herbal poultice regains an additional 2 hit points when he or she spends a healing surge at the end of the short rest.

Does the potion add extra healing to every healing surge the character spends during a short rest, or does it only add extra healing once?

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The wording is poor and unclear, unfortunately, and does not appear to have been made any clearer in any errata - the Adventurer's Vault updates and errata does not mention Herbal Poultice.

It does not appear to acknowledge the possibility that someone would spend more than one healing surge. There is no particular indication for whether the author meant you get an additional 2 hit points for each healing surge, or just an extra 2 hit points for spending any at all!

You should talk to your group about it.

Considering the tiny bonus of 2hp though, for a one-rest single-target potion, I would certainly allow it to apply to each healing surge.

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