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Rogues only get one sneak attack per turn. Which means that they can only get it once on their turn and once with their reaction (through Sentinel or a Battle Master's Commander's Strike or an Attack of Opportunity, etc.). At level 17, Scouts also get the ability, Sudden Strike, which allows them to use their sneak attack as a bonus action.

So then is three sneak attacks per round the highest number of Sneak Attacks a Pure/High Level Rogue (17 levels+) can make in one round, or is there another way to get more Sneak Attacks in one round?

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  • \$\begingroup\$ Are you allowing multi class and /or UA? \$\endgroup\$
    – SeriousBri
    Jun 24, 2019 at 18:52
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    \$\begingroup\$ or optional rules, like marking? \$\endgroup\$
    – goodguy5
    Jun 24, 2019 at 18:55
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    \$\begingroup\$ I was really thinking more along the lines of a pure rogue without optional rules, although I suppose that just "mostly" rogue (17+ levels) would count for my purposes. I saw the "Vigilant Defender" feature, and that was definitely not what I was looking for. That only leaves 2 levels for rogue, and at that point (level 19 and 20), an extra d6 would not be that big of a deal. \$\endgroup\$
    – KelvintheWizard
    Jun 24, 2019 at 19:07
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    \$\begingroup\$ And that's why putting limiters on your questions are important, folks! \$\endgroup\$
    – NotArch
    Jun 24, 2019 at 19:15
  • \$\begingroup\$ Are you interested in the maximum number of sneak attacks in a single turn, or the highest sustained per-round sneak attack count? \$\endgroup\$
    – Remilia
    Jun 25, 2019 at 12:51

1 Answer 1

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Technically, five.

Our Thief Rogue 17 (Ace) has three Battlemaster friends (Bart, Carol, and Dave). They roll initiative. Bart is first followed by Ace, then Carol, then Ace again, then Dave.

Bart uses Commander's Strike to allow Ace to sneak attack (1) with his Reaction.
Ace starts his turn, so his Reaction is ready again. Ace sneak attacks with an Attack action (2).
Carol uses Commander's Strike to allow Ace to sneak attack (3) with his Reaction.
Ace starts his turn, so his Reaction is ready again. Ace sneak attacks with an Attack action (4).
Dave uses Commander's Strike to allow Ace to sneak attack (5) with his Reaction.

This uses (abuses, really) the Thief's ability to take two entire turns during a single round, and also "steals" a reaction from the next round due to the wibbly-wobbly mechanics of how action recharge doesn't quite match up with rounds.

Mechanical abuse that doesn't quite match up with the spirit of the question would be to use a scroll of Shapechange to turn into a Marilith (credit to Miniman), which can take a reaction every turn of combat - thereby allowing one sneak attack per active combatant.

If multiclassing and having a very weak sneak attack is allowed, the possibilities are Infinite.

A Fighter (Cavalier) 18 / Rogue 2 can make an opportunity attack on every turn without using his reaction, and could feasibly sneak attack an infinite number of creatures (Arcane Gate or other mass translocation spells can provide ample space for creatures to start their turns close enough to move in/out and provoke) who choose to provoke opportunity attacks from him.

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    \$\begingroup\$ Wow... spawn camping in D&D... \$\endgroup\$
    – Nelson
    Jun 25, 2019 at 4:57
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    \$\begingroup\$ It's worth emphasizing that the 5 sneak attacks figure is only applicable to the first round and that afterward, it drops to 2 sneak attacks for a Thief Rogue as required for the 5. If the spirit of the question is more in regards to sustained per-round sneak attacks, then the Scout Rogue's 3 is the peak. In order to reach parity between the two for total, combat would have to last a minimum of 3 rounds (9 SAs each), after which the Scout is superior for sneak attack output. \$\endgroup\$
    – Remilia
    Jun 25, 2019 at 12:50
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    \$\begingroup\$ It might also be worth mentioning the Tunnel Fighter fighting style from this UA which lets you make opportunity attacks without using a reaction: media.wizards.com/2015/downloads/dnd/… \$\endgroup\$
    – DucksGoMooful
    Jun 25, 2019 at 13:35

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