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The 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. (PHB, pg 96)

and

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. (SCAG, pg 136)

This rule has been errata'd and will be changed in the upcoming Xanathar's Guide To Everything.

The way I understand them:

Step 1. identify the rules in the swashbuckler's feature

  • if your target is the only creature within 5' of you then you do not need advantage

All the other rules for the Sneak Attack class feature still apply to you

Step 2 identify "all other" rules

  • if your target is the only creature within 5' of you then you do not need advantage

  • if you have advantage [OR] you don't need advantage then you can deal an extra 1d6 damage once per turn

  • the attack must use a finesse or a ranged weapon

  • if your target has a non-incapacitated enemy that is not you within 5' of it [AND] you don't have disadvantage then you don't need advantage on the attack roll

Given: no creature other than your target is within 5 of you
Simplified: using standard logical operations

  • you don't need advantage on your attack roll

  • you can deal an extra 1d6 damage once per turn

  • the attack must use a finesse or a ranged weapon

Am I correct, a swashbuckler can sneak attack with disadvantage?
If not, please identify and explain the error?

NOTE:

  • if your target has a non-incapacitated enemy that is not you within 5' of it [AND] you don't have disadvantage then you don't need advantage on the attack roll

must be applied if and only if the non-incapacitated enemy that is not you is within 5' of your target and within 5' of you, which is typically an easy situation to fix.

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  • \$\begingroup\$ This feels a little like a contained Q&A in one question post--I suggest you consider splitting it to the naive question "can a swashbuckler..." and compose the work you've done into an answer post. This is just a personal suggestion, though--not a "moderator instruction." Honestly, there're plenty of examples of a post like this being handled either way on the site, and nothing breaks in either case. Interesting question, too--thanks for bringing it! \$\endgroup\$ – nitsua60 Aug 21 '17 at 15:04
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As of Xanathar's Guide to Everything's release, the Swashbuckler's Rakish Audacity feature has been errata'd to the following:

You also gain an additional way to use your Sneak Attack; you don’t need advantage on the attack roll to use your Sneak Attack against a creature if you are within 5 feet of it, no other creatures are within 5 feet of you, and you don’t have disadvantage on the attack roll. All the other rules for Sneak Attack still apply to you.

It now explicitly requires the Rogue to not be attacking with disadvantage to function.

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    \$\begingroup\$ You leave out one argument I think worth mentioning: that they "fix" it in one direction in XGE screams that currently it is written in the other direction. \$\endgroup\$ – nitsua60 Aug 25 '17 at 17:10
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You get Sneak Attack when you:

  • Have advantage

    OR

  • Enemy within 5 foot of target AND Enemy not incapacitated AND No Disadvantage

    OR (from Swashbuckler)

  • No creature other than target within 5 feet of you

We can safely ignore the "you don't need advantage" when writing our possibility, since if you did have advantage you would already have sneak attack.

The swashbuckler option doesn't state the "you don't have disadvantage" part, so as long as no creature other than the target is within 5 feet of you, you have sneak attack, even if you have disadvantage.

RAW, you are correct.

UPDATE: Some tweets on the subject: https://twitter.com/JeremyECrawford/status/901116196308647937

https://twitter.com/JeremyECrawford/status/901116846207713281

Apparently you should need to not have disadvantage, and this errata will be printed in Xanathar's.

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    \$\begingroup\$ It's correct RAW, but almost certainly an oversight. You'd be hard pressed to argue it's RAI. \$\endgroup\$ – r256 Aug 25 '17 at 18:04
  • \$\begingroup\$ I have a few ideas on why it could have been RAI (think the drunk Captain Jack) but you are in fact correct. Crawford announced the errata on Twitter. twitter.com/JeremyECrawford/status/901116196308647937 \$\endgroup\$ – Nicholai Bush Aug 26 '17 at 21:33
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Basic rule for sneak attack

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. PHP pg 96.

RAW you are correct if you assume the comma, and and condition are conditional on the first part of the statement versus a bad run on sentence. Read the RAW another way give the 'and you don't have disadvantage on the attack roll' as a separate conditional rule to sneak attack.

If there is Disadvantage you CAN NOT sneak attack has been the RAI in my experience.

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  • \$\begingroup\$ According to Jeremy Crawford my argument is RAW. The rule, however, is not RAI and expect to see the correction in Xanthar's \$\endgroup\$ – Nicholai Bush Aug 26 '17 at 21:29
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It is says all other rules apply their for if you have disadvantage you don't get sneak attack. The no disadvantage rule is not a conditional it is a constant rule

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