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I am making a very specific Ranger/Rogue multiclass that heavily relies on getting sneak attacks. What are some reliable ways to gain advantage on attacks in combat, especially at early levels?

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  • \$\begingroup\$ To clarify, are you looking specifically for ways to get advantage because you don't have a reliable melee fighting ally to get sneak attack for you without having to have advantage? (Because every time I've played a rogue with melee fighting allies, it's usually harder to not get sneak attack than it is to get it.) \$\endgroup\$ Jan 6, 2023 at 21:18
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    \$\begingroup\$ Possible duplicate: How can I trigger Sneak Attack without other melee combatants? \$\endgroup\$ Jan 6, 2023 at 21:20
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    \$\begingroup\$ If you have an existing party, it would be very helpful for answerers to know the makeup of races/classes/levels. \$\endgroup\$
    – NotArch
    Jan 6, 2023 at 21:22

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Since we don't know about the rest of your party, the low-hanging fruit is the Rogue's own class features.

At second level, you gain the Cunning Action feature, which lets you Hide as a bonus action. Successfully hiding from a creature (which depends on the environment and your Stealth roll) will give you advantage on attack rolls against it.

At third level, if you're using the optional rules in Tasha's Cauldron of Everything, you gain the Steady Aim feature, which lets you sacrifice your movement to gain advantage on a single attack roll.

Groody mentions the find familiar and true strike spells, available to a variant human through Magic Initiate. But a non-human can also get those spells by taking the Arcane Trickster subclass at third level; while most of your spells are limited to the enchantment and illusion schools, your cantrips are not, and you're allowed to pick one levelled spell outside those schools at third level.

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    \$\begingroup\$ The Owl familiar in particular is notorious; with a 60' flying speed and the Flyby feature (doesn't provoke opportunity attacks when flying out of opponent's reach), against melee opponents, it can spend each turn readying an action to Help with your attacks, hovering 30' up, flying in when you attack to distract them as you shank, then flying back up to 30' up after. For opponents without a ranged attack, the only counter is Readying their own action to attack as it swoops in (and if they do that, they aren't attacking the party, plus, their action is wasted if you just target someone else). \$\endgroup\$ Jan 7, 2023 at 16:48
  • \$\begingroup\$ @ShadowRanger: How does the familiar both move and Help outside its own turn? IIRC, the trick is that if can move in, Help, move out, all on its turn (not readying anything), because the Help action doesn't require you to stick around until the attack that benefits from it. (Narratively, turns sort of overlap but are also sort of serialized. And also, the distraction from a bird biting their ear can last a few seconds after the bird flies off.) Otherwise the rogue would have to Ready their attack, and make it during the familiar's turn, at the cost of their own reaction (and extra attack). \$\endgroup\$ Jan 8, 2023 at 3:24
  • \$\begingroup\$ @PeterCordes: Huh. TIL. We usually played it as movement was part of your action (whenever you took it, including after a Ready), but you're right, it's one or the other. And yeah, Help doesn't require coordination. I was way off, but the end result is that it's actually easier to do than I made it out to be. \$\endgroup\$ Jan 8, 2023 at 13:32
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There are multiple ways

The simplest, and most reliable way to enable sneak attack is to have an ally that threatens your target from within 5 feet. Outside of that, there is a number of ways to reliably get advantage as a pure rogue as explored here, including, without feats:

  • Using your Cunning Action to hide when not in plain sight and attacking from being hidden (at second level)

  • the Steady Aim rogue feature from Tasha's Cauldron of Everything (an optional rule, at third level)

  • A trained Mastiff and Animal Handling to make it attack. As it only has a few hp, this approach will become impractical after the first two or three levels.

And needing a feat, which would require you to be a variant human to get access during the first 3 levels:

  • getting a familiar, for example via the magic initiate feat, which can also give you yet another way via the true strike cantrip (you can also get them with the Arcane Trickster rogue subclass at third level, kudos to @draconis; true strike will cost your action to cast, so may not be that efficient)
  • Using a horse and the Mounted Combatant feat (although that is an unlikely tactic in most dungeon environments)
  • Using the Martial Adept feat for limited maneuvers per short rest, like Feint

Lastly, considering you are playing a ranger/rogue: one of the more effective ways if the rest of the party has darkvision is a Gloom Stalker ranger. It will give you access to Umbral Sight at third level to make you invisible in darkness — which will both give you advantage, and opponents disadvantage. At night or in dark dungeons this is a very reliable tactic, see here for an example of the results. It however will not work at the very start, as you need at least 3 levels of ranger and 1 of rogue.

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    \$\begingroup\$ It may be worth mentioning how difficult true strike is to use, especially for a melee combatant. You have to maintain concentration, it uses the Rogue's already very highly demanded bonus action, it only applies to a single attack which must be an entire round after casting the spell, and it requires a free hand for the components. \$\endgroup\$ Jan 7, 2023 at 11:38
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    \$\begingroup\$ @Exempt-Medic I added some language - TS in 5e actually costs you a full action to cast, not a bonus action. That of course is even worse than hogging your bonus action. That it only applies to one attack is probably less of an issue - of course you can sneak attack with reactions too, but normally you can only apply Sneak Attack to one attack per turn, usually on your turn. \$\endgroup\$ Jan 7, 2023 at 12:44
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    \$\begingroup\$ @goody Oh right, it's even worse than I thought XD \$\endgroup\$ Jan 7, 2023 at 15:06
  • \$\begingroup\$ For added fun, TS specifically applies to the first attack roll against the target that you make on your next turn. You can't use it for reaction attacks unless you somehow manage to have your reaction trigger during your next turn. \$\endgroup\$ Jan 7, 2023 at 15:56
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    \$\begingroup\$ Yeah, the uselessness of True Strike is well-documented (even the first use proposed on the accepted answer, attacking with a bonus action after casting it, isn't actually legal, because the spell's wording is so damn restrictive about when it grants advantage). There's a niche use case to use it for canceling disadvantage, or when a rogue can't get their sneak attack dice any other way (usually in that case you'd just attack someone adjacent to an ally twice and still do better on average), but it's really niche. \$\endgroup\$ Jan 7, 2023 at 19:21
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Since you do not specify subclasses or how many levels of each class you intend to take, I am not sure this suggestion can work for you, but I'll add it for completeness, as I do not see it mentioned in the other answers.

If you take 13 levels of rogue, and you go the arcane trickster route, you get at 3rd level:

Mage Hand Legerdemain

Starting at 3rd level, when you cast mage hand, you can make the spectral hand invisible, and you can perform the following additional tasks with it:

  • You can stow one object the hand is holding in a container worn or carried by another creature.
  • You can retrieve an object in a container worn or carried by another creature.
  • You can use thieves’ tools to pick locks and disarm traps at range.

You can perform one of these tasks without being noticed by a creature if you succeed on a Dexterity (Sleight of Hand) check contested by the creature’s Wisdom (Perception) check.

In addition, you can use the bonus action granted by your Cunning Action to control the hand.

and at the 13th it gets augmented (emphasis mine):

Versatile Trickster

At 13th level, you gain the ability to distract targets with your mage hand. As a bonus action on your turn, you can designate a creature within 5 feet of the spectral hand created by the spell. Doing so gives you advantage on attack rolls against that creature until the end of the turn.

This ties up your bonus action every turn (and 13 levels of arcane trickster), but it guarantees advantage.

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