How can I trigger Sneak Attack without other melee combatants?

Question

I am a Soulknife Rogue with a two-level dip in GOO-lock (Soulknife 6/Warlock 2). I'm taking the Armor of Shadows and Mask of Many Faces invocations. In combat situations, I find myself in both ranged and melee combat.

However, I'm in a party with a certain lack of melee combatants so I can't reliably Sneak Attack using the "target has an enemy within 5 feet" clause. While I think I'll be able to Cunning Action Hide while making ranged attacks, I'm not so certain that this tactic is viable when I'm in melee range of an enemy (i.e. within 5-10 feet).

How can I use the Sneak Attack feature without having other allies in melee to work with?

Answer 1

Steady Aim (or a horse)

Tasha's Cauldron of Everything adds Steady Aim as an optional class feature for rogue:

As a bonus action, you give yourself advantage on your next attack roll on the current turn.

Despite the name, this feature works equally well on melee attack rolls. It restricts your movement on the same turn that you use it, but that shouldn't be a problem if you are already in melee range.

Alternatively, you could purchase a mount. A camel or draft horse costs 50 gp, so it shouldn't be too hard for an 8th level character to purchase a couple (for when some inevitably get hit by fireball). Your trusty steed then serves as your adjacent ally. You could even take the Mounted Combatant feat to increase your mount's survivability, and to gain another source of advantage:

You have advantage on melee attack rolls against any unmounted creature that is smaller than your mount.

If you're not a fan of sending real mounts to their death, a bag of tricks (an uncommon magic item) is another option. Each variant allows you to summon three creatures every day, some of which are relatively sturdy (dire wolf, giant boar, giant hyena) while others aren't (weasel, rat).

Answer 2

With one more warlock level, you can get an enhanced find familiar.

Taking a third warlock level gives you access to the Pact of the Chain, which comes with an enhanced find familiar spell:

Pact of the Chain

You learn the find familiar spell and can cast it as a ritual. The spell doesn’t count against your number of spells known.

When you cast the spell, you can choose one of the normal forms for your familiar or one of the following special forms: imp, pseudodragon, quasit, or sprite.

Further, you can also take the Eldritch Invocation Investment of the Chain Master which enhances your familiar even further. One of the notable enhancements for our pursposes improves the familiar's survivability:

When the familiar takes damage, you can use your reaction to grant it resistance against that damage.

Once you have a familiar, you can use it to get advantage on your attacks via the Help action, or you can gain Sneak Attack by virtue of having your familiar standing next to your target.

Answer 3

Take the Feat "Martial Adept"

Specifically, the Feint maneuver from the battlemaster fighter. (And one other. I prefer riposte). 1/short rest you can use this to get advantage, and hence sneak attack. While limited to once per short rest, this does not depend on the 10 HP or less of a familiar, and will still be useful if another Melee character joins the rest of your party.

Answer 4

Other Rogue subclasses (Swashbuckler and Inquisitive) offer alternate ways to trigger sneak attack, but, since your build doesn't include them, you are stuck with the default ways. Therefore, besides getting another melee combatant in your party, you are limited to ways of getting advantage on your attacks.

Warlock happens to offer a few ways to get that, though they require more levels:

First of all: True Strike cantrip, not the most optimal option (takes an action, requires concentration and works for only one turn), picking pact of the tome nets you few more cantrips from any class, so it might be a neat way to get some more utility stuff along the way.

Familiars can use the Help action to grant you advantage, and there are few ways to get a familiar, either a fancy one from pact of chain, or one from a ritual (by getting pact of the tome and relevant invocation or the ritual caster feat), though familiars are notoriously squishy and even the owl familiar (that doesn't provoke AoO with its flight) still can get shot down or get eradicated by AOE spells.

Another option is the ages old Devil Sight + darkness combo. But it'll annoy rest of the team and burn your spells on that.

Then there is the Shadow Blade spell, attacks made with it in appropriate light condition (I think it's shadowy illumination) have advantage (and the weapon created qualifies for SA).

That would be all I can think of at the moment.

Answer 5

Hiding is a viable tactic in melee. Remember that the limitations for hiding are:

The DM decides when circumstances are appropriate for hiding.

...

You can't hide from a creature that can see you clearly

That means if you are fighting in darkness (and even dim light depending on the circumstances) you can hide even in melee range. You can also utilize the Darkness or invisibility spells which you may get next level. Other options include minor illusion, hiding behind other party members or enemies, or using smoke/fog.

Also keep in mind that you can hide and then ambush someone from hiding, but again it does need DM approval:

In combat, most creatures stay alert for signs of danger all around, so if you come out of hiding and approach a creature, it usually sees you. However, under certain circumstances, the DM might allow you to stay hidden as you approach a creature that is distracted, allowing you to gain advantage on an attack roll before you are seen.