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I'm looking through the PHB and I don't see any simple list of ways for a rogue to get advantage in combat. At high levels, a Rogue might have a special subclass such as Assassin that might allow advantage on attacks for sneak attack. However, if I were running a rogue I would make attacks without knowing whether I had advantage. At low levels, the only reliable way to make sneak attack seems to be to hide until the target is engaged with someone else and then stab the target in the back -- that doesn't give advantage, but it appears to be the only reliable way for a low-level Rogue to sneak attack.

Am I reading the rules correctly?

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    \$\begingroup\$ What do you consider low level? \$\endgroup\$ – Alk Sep 9 at 2:19
  • \$\begingroup\$ When I say, "low-level" I am mostly thinking 1st and 2nd in the Assassin track, and higher for other tracks. If you choose Assassin, you get: ASSASSINATE Starting at 3rd level, you are at your deadliest when you get the drop on your enemies. You have advantage on attack rolls against any creature that hasn't taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a critical hit. -- So a 3rd level Assassin has no trouble making sneak attacks frequently. \$\endgroup\$ – Long Sep 9 at 2:25
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    \$\begingroup\$ Related/helpful: "What ways exist to consistently and reliably grant my allies advantage on the attack roll?" \$\endgroup\$ – Medix2 Sep 9 at 5:38
  • \$\begingroup\$ Are you asking about any low level rogue (once defined? Are you asking about 3rd level and below, or 3-5? Or something else?) OR your low level rogue. If the latter, can you please let us know what race you are and what races/classes others in your party are? \$\endgroup\$ – NautArch Sep 9 at 13:13
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    \$\begingroup\$ Also, just so you know, the assassin Rogue's Assassinate feature only provides advantage on the first turn of combat. It's only if they haven't taken a turn that entire combat not just a single round. \$\endgroup\$ – Medix2 Sep 9 at 15:03
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Most of your sneak attacks will be triggered by an ally in melee with the target

You are reading the rules correctly: by far the most reliable way to trigger sneak attack is to attack an enemy engaged with an ally in melee. There's no need to hide or gain advantage: you can simply fight alongside an ally, or fight at range, shooting at the enemy your ally is attacking. As long as you have a melee attacker in your party, then they will be doing their best to always be in melee with at least one enemy, giving you a reliable trigger for sneak attack. This has been my experience playing in a party with a rogue, and watching/listening to D&D streams/podcasts with parties that include a rogue.

Of course, if you want to attack a specific target who isn't on the front lines and get sneak attack on that target, you're going to have a more difficult time. In that case, the next most reliable sneak attack trigger is probably to hide with your bonus action (Cunning Action, 2nd level) and then attack, gaining advantage from being unseen. Obviously this requires cover to hide behind, and you need to roll high on the stealth check, so it's less reliable than the "ally in melee" trigger, but it's still something that you can at least attempt on most combat turns, unlike most other ways of gaining advantage.

(Note: I'm not mentioning the optional flanking rules for gaining advantage, because if you're flanking then you already have sneak attack from an ally being in melee with your target.)

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  • \$\begingroup\$ Why do you say hiding would require a high roll? I assume it is about doing what is basically a hide in plain sight maneuver, but I never took the time to check the raw version of hiding in combat in 5e. \$\endgroup\$ – 3C273 Sep 9 at 2:16
  • \$\begingroup\$ I'm also curious at the number of how hight that can get. \$\endgroup\$ – 3C273 Sep 9 at 2:17
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    \$\begingroup\$ @3C273 I'm saying that the hide & attack strategy is less reliable because you must succeed at hiding to gain advantage and then succeed on the roll to hit. Succeeding on 2 consecutive rolls is usually less likely than succeeding on only one. \$\endgroup\$ – Ryan C. Thompson Sep 9 at 2:46
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    \$\begingroup\$ @3C273 You cannot hide at all in plain sight in 5e unless you're a Ranger with that specific feature (and even then it involves spending quite a bit of time to camouflage yourself), and generally speaking to be considered actually "hidden" just from breaking line of sight for a couple of seconds is not an easy thing to do (hence high stealth roll). \$\endgroup\$ – Cubic Sep 9 at 9:42
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    \$\begingroup\$ If you do not have a "melee attacker in the party", everyone will be in melee most of the time. \$\endgroup\$ – András Sep 16 at 4:24
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As you say, a rogue can use sneak attack "if you have advantage on the Attack roll" or "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 latter is by far and away the most reliable way for a rogue to get sneak attack and, except in very rare circumstances, its almost always achievable - most parties have someone who is a melee combatant who will want to get in this position.

Of course, having advantage is good because a) its advantage b) it gives sneak attack when you don't have a handy tank in melee and c) it can overcome disadvantage when you do have a handy tank in melee (because when you have both you have neither.

Here is a non-exhaustive way to get it:

  • Help by an ally within 5-feet of your target. This can be the aforementioned tank (which is probably suboptimal) or it can be a familiar or something else who doesn't have anything useful to do. Note that it doesn't have to be your familiar although if you find a way to get the Find Familiar spell, it can be.
  • Be Unseen when you attack. You can Hide using your Cunning Action once you reach 2nd level. Or a friendly spellcaster can cast Invisibility on you once they reach 3rd level but this only works once. Once they reach 7th level they can use Greater Invisibility which gives you unlimited advantage. Alternatively, you can look at methods of giving your opponent the Blinded condition.
  • Paralyze, Petrify, Restrain, Stun or render your opponent Unconscious - of course, these are all a little hard to reliably pull off for a low level party. Some are tricky for high-level parties too. A party with a rogue and a monk who uses Stunning Strike can be devastating.
  • Knock your opponent Prone and attack from within 5 feet. A grappler build is usually based around doing this so if you have one in your party this can be a very reliable method.
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    \$\begingroup\$ "Help by an ally within 5-feet of your target" looks like a waste of action, because just by being in 5ft range of said target gives OP a sneak attack. Familiars of the party are "enemies of the target" all right, and rule does not require them to be able to engage target in meele or anything. \$\endgroup\$ – Mołot Sep 9 at 6:34
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    \$\begingroup\$ Familiars staying within 5 feet of the ally usually means a dead familiar. Luckily the familiar doesn't have to stay within 5 feet after the Help action, and owls' Flyby trait means their movement doesn't provoke opportunity attacks - which is the main reason why they're such a popular choice of familiar. Also, for the Help action, the Mastermind rogue subclass can Help as a bonus action - so if there are multiple rogues in the party, one could Help the other this way. \$\endgroup\$ – V2Blast Sep 9 at 9:02
  • \$\begingroup\$ @V2Blast right, with that explanation point about help no longer looks, well, pointless. Incorporating it into this answer would improve it, I believe. \$\endgroup\$ – Mołot Sep 9 at 9:07
  • \$\begingroup\$ @Mołot If a character isn't build for combat or is out of resources, using the Help action also means improving the chance of a natural 20, doubling the damage dices of the sneak attack. \$\endgroup\$ – Nahyn - support Monica Cellio Sep 9 at 15:21
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There are two basic ways to gain sneak attack. Having advantage on the attack and having an an enemy of the target within 5ft of it.

At level 1 your choices are more limited as hiding is an action until level 2. A level 1 Bard teammate can cause a few conditions to an enemy that will grant you advantage.

  1. Glowing(Faerie Fire)
  2. Prone(Tasha’s Hideous Laughter) attacks within 5ft
  3. Unconscious (Sleep)
  4. Blinded(Prestidigitation) to snuff a torch, if you have darkvision but enemy doesn’t.

Those are just some of the conditions that can cause you to gain advantage. Other conditions that cause you to have advantage are; Paralyzed,Petrified,Restrained, and Stunned.

The Help action can also grant you advantage. Though at level 1 and 2 the Help action would most also involve having a teammate within 5ft.

I have glossed over having an enemy of the target within 5ft as the accepted answer does an excellent job of explaining.

Hiding can grant you advantage but it is dependent on a stealth check and having the proper terrain/objects to hide behind. Certain Races can make hiding in battle a lot easier. The Lightfoot Halfling Rogue can attempt to hide behind a medium sized teammate. The Wood Elf can attempt to hide while only lightly obscured.

In my last campaign I was a Rogue (Scout) and spent most of my time trying to gain advantage to increase my chances to hit/crit. Even at level 15, the level we ended the campaign, I was scheming of ways to create advantage.

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