Sneak attack on 5e with surprise?

The story is that our DM had an NPC who essentially "joined our party" but was actually an enemy rogue. In the middle of combat, the NPC ran up and attacked a party member, which the DM deemed as a surprise attack and allowed him to get sneak attack. The goal was basically to one shot a low-level character while the rest of the party was unaware.

The question is: is it normal to allow a rogue to get sneak attack in a situation like this, where the attacker isn’t hidden and otherwise doesn’t have advantage?

I know in the end it’s pretty much up to the DM’s discretion, but I can’t find where that fits in the rules, and it almost resulted in a one-hit KO.

If your target has an enemy within 5ft, can you sneak attack without using a finesse or ranged weapon?

A rogue and fighter are engaged in melee combat with a goblin. The rogue is unarmed. Can the rogue activate Sneak Attack?

The rules for Sneak Attack state:

Beginning at 1st level, you know how to strike subtly and exploit a foe’s distraction. 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.

The question arises from the difficulty in parsing the bolded sentence. I have heard 2 interpretations:

  1. You can sneak attack if (you have advantage and the attack is made using a finesse or ranged weapon) or (an enemy of the target is within 5ft, etc).
  2. You can sneak attack if ((you have advantage) or (an enemy of the target is within 5ft, etc)) and the attack is made using a finesse or ranged weapon.

The first interpretation hinges on the idea that when the second paragraph says "on the attack roll" it is still talking about the same "attack" as in the first paragraph. The second interpretation hinges on the idea that the first interpretation is bizarre and unnatural – if that was the intent, there are many ways that it could have been worded to be clearer.

Thematically, I am leaning towards the first – not having a finesse or ranged weapon shouldn’t stop the rogue from exploiting a distracted foe.

Considering RAW only (no twitter please), how should this feature be interpreted?

Best way to maximize Sneak Attack damage

Unchained Rogue

Sources allowed:

  • Core Rulebook
  • Advanced Player’s Guide
  • Advanced Class Guide
  • Advanced Race Guide
  • Ultimate Combat
  • Ultimate Magic

I’m asking for how to maximize damage output using Sneak Attack. In theory for all levels, but more specifically at level 1 through 6 or so. Whether it is using feats, magic items, (something I am overlooking?) or a combination of all of that, the objective is maximized damage output.

I don’t really want to multiclass, and want to focus on melee attacks, not ranged attacks. My character will use a shortsword.

I am just looking for maximum damage output, not how to create a ‘sneakable’ condition.

Does the Sneak Attack class feature of the Generic Classes stack with the improved and greater versions of it?

Generic Classes have the possibility to gain different class features in exchange of a bonus feat:

For the purposes of these classes, the following class features can be selected in place of bonus feats (unless noted, each may only be selected once).

The Sneak Attack class features that can be selected are:

Sneak Attack (Ex)

As the rogue ability, but +2d6 on damage rolls. Prerequisites: Hide 4 ranks, Move Silently 4 ranks.

Improved Sneak Attack (Ex)

Add +3d6 to your sneak attack damage. Prerequisites: Hide 11 ranks, Move Silently 11 ranks, sneak attack.

Greater Sneak Attack (Ex)

Add +4d6 to your sneak attack damage. Prerequisites: Hide 18 ranks, Move Silently 18 ranks, sneak attack, improved sneak attack.

Do these three class features stack together?

Can unarmed strike work with a rogue’s sneak attack?

So a situation came up last night where a player with a monk/rogue was flanking (I use the optional flanking rules to grant advantage) an enemy. He was armed with a shortsword, but even with advantage, he missed the attack roll and thus did not get to use his sneak damage.

Since he had taken the Attack action with a monk weapon (shortsword), he could make an unarmed strike as a bonus action, as granted by the monk’s Martial Arts feature. He still has advantage on that role since nobody had moved and the attack hit. But then the issue came up; is unarmed strike a finesse weapon? Is it eligible for sneak attack?

I ruled yes and allowed the sneak damage on this attack, but should I have allowed this or strictly should this not have worked?

Can an Artificer’s eldritch cannon work with the use of the Rogue’s sneak attack ability?


Sneak Attack

Beginning at 1st level, you know how to strike subtly and exploit a foe’s distraction. 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.

Eldritch Cannon

At 3rd level, you learn how to create a magical cannon. Using woodcarver’s tools or smith’s tools, you can take an action to magically create a Small or Tiny eldritch cannon in an unoccupied space on a horizontal surface within 5 feet of you. A Small eldritch cannon occupies its space, and a Tiny one can be held in one hand.

Once you create a cannon, you can’t do so again until you finish a long rest or until you expend a spell slot of 1st level or higher. You can have only one cannon at a time and can’t create one while your cannon is present.

The cannon is a magical object. Regardless of size, the cannon has an AC of 18 and a number of hit points equal to five times your artificer level. It is immune to poison damage, psychic damage, and all conditions. If it is forced to make an ability check or a saving throw, treat all its ability scores as 10 (+0). If the mending spell is cast on it, it regains 2d6 hit points. It disappears if it is reduced >to 0 hit points or after 1 hour. You can dismiss it early as an action.

Now, my question is, is an eldritch cannon counted as an enemy or not?

Is a missile deflected by a Monk/Rogue’s Deflect Missiles eligible for Sneak Attack?

Is the ranged attack resulting from a monk/rogue’s Deflect Missiles eligible to add sneak attack damage? For example, if the creature who made the initial ranged attack is engaged in melee as per the rules of Sneak Attack, or if the Monk/Rogue were to somehow have advantage on the roll, for example by way of a spent inspiration point.

I haven’t come across anything that seems to openly rule it out, but the idea of throwing somebody’s crossbow bolt back at them and doing 1d8 +3d6 damage (at Monk 14/ Rogue 6) seems a little broken to me.

How does removing crit damage for divine smite and sneak attack affect balance?

At my table, there is a house rule that divine smite and sneak attack do not recieve critical hit bonuses.

I’m worried this would heavily affect the balance of the game and am trying to petition for going back to the core rules. But the DM and a couple players believe that that would be too OP.

This is a continuation of a previous question.

Can unseen servant trigger sneak attack with a rogue

Say a rogue is fighting an enemy, and either they or someone else has unseen servant and they sent it to engage that enemy. Can the rogue now use a sneak attack?

Unseen servant is very clearly described as an entity that shouldn’t be used or useful in combat, this seems to go against that idea. In the same vein, rogues get sneak attack when there are others supporting them, again, the idea of them (if multiclassing) using a spell for this seems to be more of a loophole than a valid strategy.