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I've recently started DM-ing 5e for the first time.

Rogue's sneak attack says that the sneak attack bonus damage is applied once per turn to a selected attack the Rogue has an advantage on.

DMG, p.251 - as admittedly optional rule - states that flanking gives advantage. I'm willing to allow it, because it just makes a lot of sense, especially if the enemy is exactly between two players.

The situation: In a narrow corridor a Rogue and druid stand next to each other, together occupying corridors width. A monster (medium size) approaches them and starts attacking. Rogue uses his move action to move behind him (never leaving enemy's reach, so no AoO), and therefore they're flanking - sandwiching - the monster. By flanking rules, they now have advantage on the attack rolls, and Rogue can apply his sneak attack damage.

My question: is that scenario correct, or am I missing some important rule that makes this invalid? I don't mind my players having a lot of damage output, I think that it makes sense that a surrounded enemy is getting stabbed to death, but I don't want all my calculated encounters be completely out of balance now.

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    \$\begingroup\$ Where exactly does your confusion lie? You seem to understand both flanking and Sneak Attack so I'm not entirely sure where your confusion is coming from? If the question simply is an affirmation that your reading the rules correctly that's fine, I'm just curious. \$\endgroup\$ – Purple Monkey May 1 '15 at 9:24
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    \$\begingroup\$ I've read both manuals, I've read a lot of SE/Reddit posts about rules, but there is just a lot of them, and my lack of experience makes me quite uncertain whether I'm not missing anything. So yeah, I wanted someone more experienced to check my understanding and call out anything I've missed :) \$\endgroup\$ – Gerino May 1 '15 at 9:42
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    \$\begingroup\$ Your situation is only valid in the event of multiple people ganging up on a single monster I think. (Which in real life is also a great way to get backstabbed) If you have multiple monsters, the rogue is going to be provoking AoO's from other monsters. This is why 9 out of 10 evil dungeon overseers recommend the 'buddy system' for their employed monsters. Dungeon work safety is important. \$\endgroup\$ – Theik May 1 '15 at 11:24
  • \$\begingroup\$ @Theik - I thought I was being evil sandwiching my party between two monsters in a narrow corridor. I forgot that dividing 4 adventurers between 2 monsters gives two sandwiched monsters instead :D \$\endgroup\$ – Gerino May 1 '15 at 13:26
  • \$\begingroup\$ It's been this way for multiple versions: Gang up on a monster and you generally get sneak-attack damage on it. \$\endgroup\$ – Loren Pechtel May 1 '15 at 22:33
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Yes, you read the rules correctly.

Please note that in D&D some powers are very powerful in some levels, but even out at later levels. Sneak attack is pretty powerful in the first few levels, but later on, when people get more attacks and special attacks and spells, it is not as powerful as it seems at level 1 or 2.

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  • \$\begingroup\$ Thanks! I was mostly doubtful about rogue casually walking past an enemy and commencing stab-fest. Of course in RP narration that would be a graceful movement rather than a stroll, but still sounded a bit fishy :) \$\endgroup\$ – Gerino May 1 '15 at 9:44
  • \$\begingroup\$ @nvoigt is spot on with this, but just to clarify - I think that game balance expects a Rogue to be using Sneak Attack quite a lot in order to keep up with the damage output of other classes, so while quite effective at lower levels it quickly just becomes the mainline attack option. \$\endgroup\$ – James Alday Aug 26 '16 at 13:31
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The scenario you've provided is correct.

Flanking grants advantage to melee attack rolls and Sneak Attack can be applied if the rogue makes an attack roll with advantage. However there seems to be one slight thing you're overlooking.

A rogue can choose to apply Sneak Attack if they have advantage or if an enemy of the target is within 5 feet of the target and isn't incapacitated and the rogue doesn't have disadvantage.
If the scenario is as such (X=floor, Y=enemy, A=Rogue, and B=Druid and enemy of Y):

xx
xx
xY
AB

than the rogue can choose to apply Sneak Attack without needing the advantage gained by flanking. The only downside here though is that neither the rogue nor the druid has advantage on their melee attack rolls so flanking would still be preferable in any case.

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  • \$\begingroup\$ Oh, you're right! I've missed it completely! Thanks! \$\endgroup\$ – Gerino May 1 '15 at 13:24
  • \$\begingroup\$ I just noted the same second part in comments on the question (deleted once I saw this answer that explains it better). The optional rule for flanking does not add new sneak attack opportunities, but does change what the best tactics are for melee - as it is easy to move around opponents in 5E, it can also make Advantage happen more often in general, which the OP may or may not want. \$\endgroup\$ – Neil Slater May 1 '15 at 13:34

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