Sneak Attack Tactics for D&D 5e and 5.5e

Analysing the rogue’s unique damage mechanic and how you can maximise its use.

How does sneak attack work?

Let’s start with how it’s described in the actual feature. Below is the text on sneak attack from the 2014 version the Player’s Handbook:

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 amount of the extra damage increases as you gain levels in this class, as shown in the Sneak Attack column of the Rogue table.

Player’s Handbook (2014) p96

The 2024 version of the rogue changes the language slightly and clarifies that the damage type of the sneak attack is the same as the weapon’s, but basically works in the same way.

Essentially, a sneak attack:

• Can be used once per turn
• Deals extra damage according to your rogue level starting at +1d6 and increasing every 2 levels to +10d6

But there are some prerequisites. You must:

• Hit with an attack
• That attack must be made with a finesse or ranged weapon
• The attack must have advantage
• Or it must be made against a creature that’s within 5ft of another of its enemies (or one of your allies in the 2024 rules) that isn’t incapacitated
• You can’t have disadvantage on the attack roll

What’s obvious is that sneak attacks are powerful damage dealers and landing them is crucial for a rogue to stay relevant in combat in the absence of spells or extra attacks. 1d4/6 + dexterity modifier might be OK at level 1, but by level 5, without sneak attack, rogues will quickly become irrelevant in battle.

Making sure you land a sneak attack

Obviously landing a sneak attack is really important for a rogue. But making sure you can land a sneak attack can require a bit of forward thinking. Fortunately, there are a bunch of ways to do this.

Gaining advantage

Gaining advantage is probably the most straightforward way to be able to land a sneak attack. Fortunately, there are a bunch of ways to do this, and even more in the 2024 rules.

While I can’t cover every possible method of gaining advantage, I’ll try and cover some of the more common or easy to work options. I’ve also split these into options that work for both editions of 5e and those that only work for the 2014 or 2024 editions.

Both editions

• Knocking prone: If you make a melee attack against a creature that’s prone, you’ll have advantage on that attack. Just be aware that ranged attacks against a prone target have disadvantage.
• Steady aim: At level 3, you gain a feature that lets you grant advantage to your attacks with a bonus action as long as you don’t move that turn. For 2014 rogues, this is an optional feature from Tasha’s Cauldron of Everything that I’d strongly recommend using.
• Assassins using assassinate: Assassins have advantage on attack rolls against creatures that haven’t taken a turn yet.
• Aracne tricksters using versatile trickster: Arcane tricksters in both editions can use their mage hand to grant advantage on attack rolls, though both do it in slightly different ways.
• Hiding: When you’re unseen by an enemy, you have advantage on attack rolls against them. This can come by simply taking the hide action, or become invisible (the 2024 rules kind of merge these effects anyway).
• Help action: An ally with little else they can do on a turn could use the help action to grant you advantage. Hobgoblins and masterminds can do this as a bonus action.
• Blindness: If you can somehow blind a creature, then attacks against them have advantage. Some methods of doing this require obscuring an area in fog or darkness (like with the fog cloud or darkness spells). When this is the case, you may need a method of blindsight to help you see here. The 2024 skulker feat can help with this.
• Stunned condition: If you or an ally can cause the stunned condition through something like a monk’s stunning strike, then you can have advantage against those enemies.
• A bunch of other conditions too: In fact restrained, paralyzed, petrified and unconscious will all have the same effect too.
• Spells: Some spells might grant advantage on your attacks or attacks against certain creatures. For example, faerie fire grants advantage against certain targets, blindness/deafness can cause the blinded condition and invisibility causes the invisible condition giving you advantage on attack rolls.

2014 only

• Flanking: An optional rule that grants advantage when enemies are flanked from different sides.
• Inspiration: Grants advantage on a d20 roll which could be an attack roll. While inspiration in the 2024 rules is more common (now known as heroic inspiration), it doesn’t grant advantage, instead it gives a reroll after you see the result of the roll. This is usually better, but not for a rogue trying to get sneak attack.

2024 only

• Topple weapon mastery: This will allow weapon attacks to knock enemies prone. You’ll either need an ally to do the knocking prone, or you’ll need to be dual wielding to get another attack to apply this and then benefit on the subsequent attack.
• Vex weapon mastery: Similarly here, you’ll need an attack to set this up, but your follow up attack will have advantage. You may need an ally or a spare attack to get the benefits of this in the same turn, but it could also be setup for your next turn.
• Cunning strike trip: Similar to the topple mastery, you can use cunning strike trip to knock an enemy prone at the expense of a bit of sneak attack damage. If someone can grapple them while prone, they’ll stay down for your next attack too.

Sneak attack without advantage

Attempting a sneak attack with advantage will always be superior as you have a better chance of hitting.

However, if you are not able to gain advantage on an attack, perhaps because your bonus action is needed for something else or you have disadvantage from some other effects, then you can still land a sneak attack. You just need an ally to be next to your target. This may require a bit of coordination, but still gives you the chance to land your all important sneak attack.

Increasing the odds of landing a sneak attack

Landing a sneak attack is so important that you want to make sure you put effort into making it as reliable as possible. Obviously gaining advantage on attack rolls accomplishes this to a large extent, but there are more ways that we can up the odds of landing a hit.

Dual wielding

One way that you have full control over this is by using two weapons allowing you to make an offhand attack with your bonus action. Now you have 2 attacks to attempt a sneak attack rather than one, doubling your chances of landing a successful attack and potentially allowing some setup of advantage for subsequent attacks.

This isn’t a perfect solution though. This second attack will require your bonus action which often, you’d be using to gain advantage in the first place (through something like steady aim or the hide action). It’s great though if you have other methods of gaining advantage.

The 2024 rules do help here. If you take the nick weapon mastery option on something like a dagger, then you can make 2 attacks with your action, leaving your bonus action free for other important rogue things. You could also double down on more attacks too if you take the dual wielder feat, which would occupy your bonus action, but means a third attack each turn if your first 2 fail to land a sneak attack.

Allied support

Allies can help here too, especially if they have features that can enhance attack rolls. Some examples of these include:

• Bardic inspiration (bard): Rogues are a great choice for applying bardic inspiration as they can use this to enhance their attack rolls to up the odds of landing a sneak attack.
• Portent (diviner wizard): Diviners have a pair of d20 they can use to change the d20 roll of another creature. If these are quite high, then they could replace a poor attack roll for a rogue to help them land a sneak attack.
• Experimental elixir (alchemist artificer): The boldness elixir will add D4 to attack rolls.
• Bolstering magic (path of wild magic barbarian): Can add d3 to attack rolls.
• Cosmic omen (circle of stars druid): Can use a reaction to add d6 to a d20 test.
• Bend luck (wild magic sorcerer): Can use a reaction to add 1d4 to d20 tests.
• Emboldening bond (peace domain cleric): Once per turn, affected creatures can add 1d4 to attack rolls they make.
• Bless spell: Adds 1d4 to attack rolls.
• Elemental and magic weapon spells: Both add 1-3 to attack rolls depending on the level at which they’re cast.

Making 2 sneak attacks per round

You may be thinking that 1 sneak attack sounds great, but 2 sneak attacks would be even better. Well I have good and bad news for you. The bad news is that you definitely can’t make more than 1 sneak attack on your turn. However, the good news is that the 1 sneak attack limit is per turn, not per round. This means that it is possible to land more than 1 sneak attack per round (by doing so on other creature’s turns). Unfortunately, without effort, preparation and a perhaps some teamwork, this is unlikely to happen very often.

Realistically, you need to be ensuring that your rogue can make reaction attacks as much as possible while fulfilling the other requirements of a sneak attack (advantage or an ally next to your target). This isn’t particularly easy, but here are a few ways you can work it into your combat.

This does mean you’ll need to keep your reaction free (rather than using it on something like uncanny dodge) and will likely need to go for a melee build that is happier staying in danger.

Below are some ways you can integrate reaction sneak attacks into your rogue’s combat:

• Dissonant whispers: If an ally takes this spell, they can try and force a creature next to the rogue to move away with their reaction, allowing the rogue to make an attack of opportunity.
• Order domain cleric: If an ally is an order domain cleric, they can use voice of authority from level 1 to target the rogue with a spell which then allows them to use their reaction to make an opportunity attack.
• Sentinel feat: If you grab the sentinel feat, you can make an opportunity attack against anyone that attacks a nearby ally or takes the disengage action.
• Battle master fighter: If you have an ally playing a battle master, they can use commander’s strike to give the rogue an attack with their reaction.
• Superior technique fighting style: As with the battle master, anyone taking the superior technique fighting style can also take commander’s strike and do the same thing. Alternatively, you could take this fighting style through the martial adept feat and take the riposte option for reaction attacks when missed by an attack.
• Haste: If you can get haste cast on you, then you’re able to make an attack with one action then ready and attack with the other action which can be triggered on another creature’s turn.
• Action surge fighter: A 2 level dip in fighter will also get you action surge allowing you to do a similar thing with your additional action.

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Sneak attack is a great feature, even if the rogue is slightly on the weak end of classes in combat (especially in D&D 2024). But knowing how to really maximise on sneak attacks goes a long way to making up the difference in power. There are other similar ways to maximise on sneak attack. Let me know any others you’ve found in the comments below.

Spotlight on D&D 2024