You’re standing in a damp dungeon corridor. The Paladin is clanking around in plate armor, basically ringing a dinner bell for every goblin in a three-mile radius. You? You’re pressed against the cold stone, waiting. The moment the Fighter engages that bugbear, you strike. You roll a handful of d6s, and the DM’s jaw drops. That’s the dream, right? But honestly, rogue sneak attack 5e is one of the most misunderstood mechanics in Dungeons & Dragons. I’ve seen tables grind to a halt because nobody can agree on whether the Rogue actually "hid" or if "flanking" is a real rule or just a popular house rule from 3.5.
It’s not just about being "sneaky." In fact, the name is kinda a lie. You don't need to be sneaking to use it. You just need to be tactical.
Most people think you need to be draped in shadows, whispering "nothing personal, kid" to get those extra dice. Nope. The Player’s Handbook is actually pretty specific, but the wording can be a bit dense if you're just skimming during your turn. Basically, you’re looking for an opening. You’re exploiting a distraction. If your buddy is within 5 feet of the monster and isn’t incapacitated, you get those dice. It doesn’t matter if you’re standing in broad daylight yelling at the top of your lungs.
The Core Mechanics of Rogue Sneak Attack 5e
Let's break down the actual math and the "permission slips" you need to trigger this feature. You get to add extra damage—starting at $1d6$ and scaling up to $10d6$ at level 19—to one creature you hit with an attack roll. But there are hard requirements.
First, the weapon. It has to be a finesse or a ranged weapon. You can’t sneak attack with a longsword, even if you’re using your Dexterity (which you can’t do anyway unless you're a Monk, but let's stay on track). You can’t sneak attack with a heavy crossbow using Strength. It’s about precision, not brute force. If you’re swinging a rapier or firing a shortbow, you’re in the clear.
Second, the "Why." You need one of two things:
- Advantage on the attack roll. This could come from being hidden, the Guiding Bolt spell, or the enemy being prone (if you’re within 5 feet).
- An ally within 5 feet of the target. This is the bread and butter for most Rogues. If your Barbarian is up in the enemy’s face, you get Sneak Attack. The ally doesn't even have to do anything. They just have to be a threat that the enemy is worried about.
Wait. There’s a catch. Even if you have an ally there, you can’t have disadvantage on the roll. If you’re poisoned or trying to shoot a bow while a different enemy is standing next to you, no Sneak Attack for you. Disadvantage cancels out the opportunity, even if you have an ally helping.
The Myth of "Once Per Turn"
This is where the real pros separate themselves from the amateurs. The rule says "once per turn." It does not say "once per round."
Read that again.
In D&D 5e, a "round" is the whole cycle of everyone’s initiative. A "turn" is your specific slice of that round. If you can find a way to attack on someone else’s turn, you can Sneak Attack again. The most common way to do this is with an Opportunity Attack. If a monster runs away from you and you stab them with your reaction, and you have advantage or an ally is nearby? Boom. Second Sneak Attack in the same round.
Some high-level players multiclass into Fighter just for Action Surge, or they beg the party’s Haste-caster for an extra action. You use your main action to "Hold Action" (triggering on someone else's turn) and use the Haste action to attack on your own turn. It’s a bit sweaty, sure, but it doubles your damage output.
Why Advantage Isn't Everything
I see a lot of new players spend their entire turn trying to "Hide" using their Cunning Action just to get advantage. It’s a valid strategy, but often it’s a waste.
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If your Fighter is already engaged with the boss, you already have Sneak Attack. Using your bonus action to hide just to get advantage on a single roll is sometimes less effective than, say, using two weapons. If you use two daggers, you get two chances to hit. Since you only need to hit once to proc your Sneak Attack damage, the math often favors "more swings" over "one swing with advantage."
Of course, the Steadfast Aim feature from Tasha’s Cauldron of Everything changed the game. Now, you can use a bonus action to give yourself advantage as long as you don't move. It’s a godsend for snipers. But it’s boring. It turns the Rogue into a stationary turret.
Subclasses That Break the Rules
Every rule has an exception, and D&D subclasses love to mess with the rogue sneak attack 5e flow.
Take the Swashbuckler from Xanathar’s Guide to Everything. These guys are the duelists. They don’t need an ally. If they are within 5 feet of an enemy and no other creatures are within 5 feet of them, they get Sneak Attack. It’s perfect for the lone wolf who wants to 1v1 the big bad.
Then there’s the Inquisitive. They use an Insight check against an enemy’s Deception (Insightful Fighting). If they win, they get Sneak Attack on that target for a full minute, regardless of whether they have advantage or allies nearby. It’s basically "I’ve figured out your fighting style, and now I’m going to poke every hole in your armor."
- Arcane Tricksters use Find Familiar. An owl familiar can use the "Help" action and then fly away without taking opportunity attacks (thanks to Flyby). It’s basically a portable Sneak Attack generator.
- Assassins get automatic crits on surprised creatures. When you crit, you double all the dice. Yes, including the Sneak Attack dice. Rolling $4d6$ at level 3 feels like cheating. It isn't.
Common Pitfalls and DM Arguments
You’re going to run into a DM who thinks Sneak Attack is "overpowered." It isn't. Rogues are designed around this. While a Paladin can smite and a Fighter can attack four times, the Rogue gets one big hit. If you miss that hit, your total damage for the round is zero.
One big point of contention is visibility. If you’re hiding in dim light, can you Sneak Attack? According to the Player’s Handbook (page 177), the DM decides when circumstances are appropriate for hiding. However, the Skulker feat or being a Wood Elf (Mask of the Wild) makes this way easier.
Another one: Ranged attacks in melee. If you're using a bow and an enemy is standing next to you, you have disadvantage. Remember what I said earlier? Disadvantage kills Sneak Attack. Even if another ally is helping you, you're too distracted by the guy in your face to find the "weak point." Switch to a rapier.
How to Maximize Your Damage Every Session
If you want to actually be effective, you need to think about your positioning. Don't just run in. Wait for the heavy hitters to plant themselves.
Look for ways to trigger reactions. The Sentinel feat is incredible for Rogues. If a monster attacks your friend instead of you, Sentinel lets you stab them as a reaction. Since it's not your turn, that's another Sneak Attack.
Also, don't ignore poisons. A lot of Rogues forget they can apply basic poison to a weapon. It’s a low DC save, sure, but every bit of damage adds up when you’re the party’s primary "single-target deleter."
Actionable Steps for Your Next Game:
- Check your weapon tags. Ensure you are using "Finesse" or "Ranged." (No, a high-Dexterity jump with a longsword doesn't count).
- Coordinate with the tank. Ask the Barbarian or Paladin who they're targeting. Stick to them like glue.
- Track your "Once Per Turn." Always look for Opportunity Attacks. It is the most consistent way to double your DPR (Damage Per Round).
- Use Cunning Action wisely. Don't just Disengage. Use it to Dash into a better position where an ally is already standing.
- Understand the "Unseen Attackers" rule. If the enemy can't see you, you have advantage. This applies to heavy fog, darkness (if you have Darkvision and they don't), or just being invisible.
Basically, the Rogue isn't a front-line fighter. You're a scavenger. You're looking for the moment of weakness. When the dragon turns its head to breathe fire on the Wizard, that's when you put the dagger in the soft spot under the scales. That's the essence of the mechanic. It’s not about being a coward; it’s about being the most efficient killer at the table.
If you master the timing of your reactions and the positioning of your allies, you'll stop asking "Can I sneak attack?" and start telling the DM "I'm rolling 20 dice now."