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This question is somewhat related to Can you get Sneak Attack with any weapon as a Swashbuckler?

One of my players is a Swashbuckler Rogue, and we debated if he could use the Sneak Attack on every attack with the Rakish Audacity ability (from the Sword Coast Adventurer's Guide):

In addition, you don't need advantage on your attack roll to use your Sneak Attack if no creature other than your target is within 5 feet of you. All other rules for the Sneak Attack class feature still apply to you.

Here are the Sneak Attack rules:

Once per turn, you can deal an extra 1d6 damage to one creature you hit with an attack if you have advantage on the attack roll. The attack must use a finesse or a ranged weapon. You don’t need advantage on the attack roll if another enemy of the target is within 5 feet of it, that enemy isn’t incapacitated, and you don’t have disadvantage on the attack roll

So, the original ability removes the advantage requirement if an ally is within 5 feet of the target, and the Rakish Audacity removes the advantage requirement if no other creature is within 5 feet of the Swashbuckler.

Does it mean that the Swashbuckler can use Sneak Attack every turn on an isolated target ? (assuming he uses a finesse weapon, of course)

PS: the party is now level 6, and with this ability, the rogue really does a lot of damage compared to his fellows (paladin, cleric, fighter and wizard.. ok, maybe not the wizard, but still)

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No, because the two conditions do not encompass every possibility.

If the Swashbuckler (S) has interposed himself between an Ally (A) and an Opponent (O). Each occupies a single five by five square.

Such as:
ASO

In this scenario, an ally is within 5 feet from the swashbuckler, but there isn't an ally within 5 feet of the opponent. Lacking an additional effect that will provide advantage to the Swashbuckler, Sneak Attack won't be available.

Similarly, if the Swashbuckler (S) is facing two Opponents (O and X), there are several configurations in which Sneak Attack isn't available.

To summarize, the following conditions will prohibit you from using Sneak Attack, assuming there isn't an external effect providing Advantage.

  • Swashbuckler is within 5 feet of more than one hostile creature or character.
  • Swashbuckler is attacking the target at melee range and a friendly character or creature is within 5 feet of him but isn't within 5 feet of the target.

Per a twitter post by Jeremy Crawford, Rules as Intended want the Swashbuckler to be within 5 feet of the target. In effect, Rackish Audacity should be written with "except" instead of "other."

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    \$\begingroup\$ I edited the question title to be specific for isolated targets, so the first point isn't relevant anymore. Assuming the party lets the rogue apply his "melee hit and run" strategy, he could use Sneak Attack every time, I guess ? \$\endgroup\$
    – Yotus
    Jan 7, 2016 at 8:21
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    \$\begingroup\$ @Yotus Question doesn't define what isolated means, thus the summary of case where sneak account can't be used. If conditions are maintained such that these cases are avoided, then sneak attack can be used during every Swashbuckler turn and in Opportunity attacks during the turns of other creatures or characters. \$\endgroup\$
    – Drunk Cynic
    Jan 7, 2016 at 13:58
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It's more about the Rogue being (almost) isolated

As a Swashbuckler you get to use Sneak Attack if at least one of the following apply:

  • No creature (ally or enemy) but the target is within 5ft range of the Rogue
  • A creature hostile to the target is within 5ft range of the target and the Rogue doesn't have disadvantage on the attack roll
  • The Rogue has advantage on the attack roll

As always, you get to use Sneak Attack only once per turn.

If your question was supposed to be Can a Swashbuckler always use Sneak Attack on a melee attack?, then the answer is a clear No, as there are still constellations in which none of the mentioned conditions apply.

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  • \$\begingroup\$ @DrunkCynic can you point me to where it says that a rogue gets Sneak Attack if no creature is within 5 feet of said rogue? \$\endgroup\$
    – Purple Monkey
    Jan 7, 2016 at 14:47
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    \$\begingroup\$ @PurpleMonkey Reading of Rakish Audacity, as cited by the Question, if the rogue is attacking with a ranged weapon or a melee finesse weapon with reach, such as the whip. Since it says "no creature other than your target" rather than "no creature except your target," it doesn't read as requiring your target to be within 5 feet of you. \$\endgroup\$
    – Drunk Cynic
    Jan 7, 2016 at 15:18
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    \$\begingroup\$ @DrunkCynic I really don't see how it's read that way. To me, "no creature other than your target" means "no creature except your target". \$\endgroup\$
    – Purple Monkey
    Jan 7, 2016 at 15:31
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    \$\begingroup\$ @PurpleMonkey Seems RAI agree with your, but in that case I would have written it differently. Googling demonstrates Jeremy Crawford has answer this: twitter.com/jeremyecrawford/status/663514748785262592 \$\endgroup\$
    – Drunk Cynic
    Jan 7, 2016 at 16:03
  • \$\begingroup\$ @DrunkCynic I can see how you would read it that way, however, to me it's ambiguous. It can have our meaning just as well as yours, without any interpretation involved, and not exclusively yours. Anyway, thanks for finding that tweet to clear that up. \$\endgroup\$
    – ammut
    Jan 8, 2016 at 7:35
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Yes

There is no reason for the swashbuckler not to get a sneak attack every round if their target remains isolated and nothing hinders the swashbuckler.

The damage from a sneak attack, is comparable to the damage done by a fighter with multiple attacks or heavy weapons.

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    \$\begingroup\$ Not true. The question was if the character can get Sneak Attack if the Target is isolated, to which the answer is not always yes; the Swashbuckler itself may not be isolated, which would mean the Swashbuckler may not get Sneak Attack. \$\endgroup\$
    – Mag Roader
    Jan 7, 2016 at 16:50
  • \$\begingroup\$ @Mag Roader: I don't see where it is written that the Swashbuckler must be isolated for the Sneak Attack to work ? \$\endgroup\$
    – Yotus
    Jan 8, 2016 at 6:48
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    \$\begingroup\$ According to the quote in the question: "if no creature other than your target is within 5 feet of you." So there's a case where the Swashbuckler's target is isolated, but the Swashbuckler is not isolated, so the Swashbuckler does not get sneak attack. \$\endgroup\$
    – Mag Roader
    Jan 8, 2016 at 20:54
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    \$\begingroup\$ @MagRoader If there is somebody else around, then they aren't isolated. I'm very confused by the reading of the question that way. \$\endgroup\$
    – GMNoob
    Jan 9, 2016 at 22:13
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Toujours l'Audace

[...] In addition, you can use Sneak Attack with any melee attack made against a target that has none of your allies adjacent to it.

Waterborne v3

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  • \$\begingroup\$ Apparently that's the unpublished version; the revised version in the SCAG apparently says: "Starting at 3rd level, your unmistakable confidence propels you into battle. You can add your Charisma modifier to your initiative rolls. In addition, you don't need advantage on your attack roll to use your Sneak Attack if no creature other than your target is within 5 feet of you. All the other rules for the Sneak Attack class feature still apply to you." \$\endgroup\$
    – V2Blast
    Dec 14, 2017 at 10:16

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