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When my Rogue uses Circling Predator, he gets to attack twice:

Hit: 1[W] + Dexterity modifier damage.
Effect: You can shift 1 square and must end adjacent to the target. Then make a secondary attack against it.
Secondary Attack: Dexterity vs AC
Hit: 1[W] + Dexterity modifier damage, and you gain combat advantage against the target until the end of your next turn.

If the Rogue has combat advantage and no special feats does he gain sneak attack damage for each separate attack?

Or can sneak attack only be applied to one attack per turn/round?

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You may only apply Sneak Attack once per turn

However, you may apply it whenever you wish in that turn, so long as you meet the conditions:

When you make an attack with a light blade, a hand crossbow, a shortbow, or a sling and hit an enemy granting combat advantage to you, that enemy takes extra damage based on your level (see the Sneak Attack table). You can deal this extra damage only once per turn.

Given that all uses of powers and class features tend to be optional unless otherwise stated, there is no reason why you cannot take SA on either attack. If you have Slaying Action you may apply it on a second action granted by sneak attack. There are a number of powers that grant sneak attack damage as well.

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According to page 117 of PHB1 under Sneak Attack

Once per round, when you have combat advantage against an enemy...

So you'd only get sneak attack damage for the first attack that hits.

If you are to go with the errata at WotC website, you may deal damage once per turn.

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  • \$\begingroup\$ Could a Rogue choose to forgo sneak attack damage on the first hit and take it on a later hit? \$\endgroup\$
    – Mark Rogers
    Apr 20, 2011 at 21:57
  • \$\begingroup\$ Also according to one errata you can deal extra damage once per turn instead of once per round. "Sneak Attack Page 117: The feature now lets you deal extra damage once per turn instead of once per round." \$\endgroup\$
    – Mark Rogers
    Apr 20, 2011 at 22:00
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    \$\begingroup\$ You decide whether to apply the extra damage after making the damage roll. Presumably, you could opt not to in the hope that you hit with another attack that turn. Not clear if you get to reroll the sneak attack damage in that case; I would guess not. \$\endgroup\$
    – okeefe
    Apr 20, 2011 at 22:08
  • \$\begingroup\$ Player's Handbook Errata(pdf) on wizards of the coast website. \$\endgroup\$
    – Mark Rogers
    Apr 20, 2011 at 22:08
  • \$\begingroup\$ @Mark Ah ha! I have edited my answer to include the errata. Thank ya for catching that! \$\endgroup\$
    – The Jug
    Apr 21, 2011 at 0:23
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Yes (to either attack but not both)
As everyone has pointed out, you can get sneak attack once you have combat advantage but only once per turn.

No (to the second attack)
If your combat advantage comes from being hidden or invisible, you cannot apply your sneak attack to your second attack because you will not have combat advantage after your first strike.

Might I suggest Quickhit Bracers (Adventurer's Vault pg118) and Shadowdancer's Gloves (Adventurer's Vault 2 pg105) that will give you an extra 2d6 of damage for that turn.

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