Help in getting a second sneak attack

[CapnZapp]

I'm the DM and I'm having quite the conundrum.

My Rogue player is hopelessly behind in damage (the rogue class really is impossible to min-max the way the others min-max other classes), and even though I'm the DM I'm having trouble finding was to help.

My goal is specifically to open up the window of a second helping of sneak damage.

This is because I believe that would gel with my player's preferred playing style, which is very straight-forward.

The entire business of optimizing opportunity attacks does not seem to engage him, and as far as I'm aware that's the only legit way of getting a shot at a second sneak.

Yet, he's clearly disappointed everyone else outdamages him.

We're playing a game with items, feats and multi-classing; and the rogue simply doesn't keep up.

So now I wonder, what canon or even semi-canon ways are available to me to introduce a magic item that helps with this situation, drawing from both 5e and 3e magic items.

Let me give you an example: the dancing weapon. In 3e it wasn't a stretch to allow this to make a sneak attack. But in 5e; not only is it outruled by RAW, the dancing attack happens on the Rogue's turn, so it really is a non-starter.

Any other item or effect I could use?

Ideally, I'm looking for another way to make an out-of-turn attack other than the opportunity attack (since this seems to be a difficult or underhanded concept).

But in a pinch a magic effect that triggers an OA would do, since that opens up the possibility of a second helping of sneak damage, which would do wonders helping this character stand his ground against the rest.

The Rogue really is frustratingly underpowered for such a squishy chassi; there are no feats, no class abilities and no DMG items that increase sneak damage!

(We jointly decided against the Assassin subclass - it simply will not enter play often enough to be justified)

Anyway, any suggestions, any old d20 systems mastery, would be appreciated ☺

 

[TwoSix]

Are you looking for something already present in the existing rules? Or methods that existed in previous versions that could be house-ruled into a 5e version to help the rogue player?

When you say "optimizing opportunity attacks", do you mean current methods like battle master maneuvers or Sentinel feat to gain off-turn reaction attacks? BM 3 (or 5)/Rogue X is probably my favorite overall Rogue build, but you could easily take the feat that gives a limited pool of maneuver points.

If you're using UA, the Tunnel Fighter fighting style would work.

 

[Wiseblood]

What is in the party that is outshining the rogue?

 

[transtemporal]

What is in the party that is outshining the rogue?

The guys with SS and GWM!

Seriously though, to maximise his dps he needs to get in another sneak attack via the battlemasters manoeuvre Commanders Strike. Grants an attack via a reaction. Not sure if there are other abilities that grant attacks on a reaction.

 

[mellored]

How about giving him the booming blade cantrip / green flame blade?

"Thunder and Fire: This pair of daggers let's you cast the booming blade and green flameblade cantrips. Dexterity is your casting modifier.
In addition, if you throw one of the daggers while holding the other, the thrown one reapepars in your hand at the end of your turn. If the daggers are ever sepearted, they teleport to eachother."

 

[Prakriti]

Why does it need to be Sneak Attack damage? Why does the item need to be from the DMG rather than one you've created yourself?

Also, is the Rogue so underpowered that a Flame Tongue weapon won't make up the difference in DPR? Or a Vorpal sword?

 

[BookBarbarian]

Scout gets a second sneak Attack, but it's at high level.

As far as magic items go you can make one to do whatever you want.

 

[Tales and Chronicles]

I was just looking at the 4e assassin's class powers, and there was one power who allowed the assassin to force a shadow to betray its ''owner'' to allow flanking and double tap attacks for a short time. Maybe one item that does the same; I'd look at the Trickery Cleric clone feature with a 1/short rest or 1/day recharge rate depending on how many time you want him to sneak attack.

Gloves of Unfaithful Shadows
Wondrous Item, Very rare, Rogue only, require attunement.
It is said that the gnome wanna-be adventurer Hurton Papernerves was such a coward that his own shadow grew tired of him and departed on her own adventures. Tales said that she attached herself to many great adventurers and even created her own group of independent shadow adventurers. Tired of seeing his own shadow out-staging him in the adventuring domain, the gnome ask a passing enchanter to create a pair of gloves he would used to hold the shadow in place. To his dismay, the shadow learned of his plan and succeeded in stealing the gloves for herself, using them to capture the shadow of Hurton's wife before setting off in the night.

Once per short rest you may grab the shadow of a foe as a bonus action. For 1 minute, the shadow fight against its owner, making one attack sharing the Sneak Attack feature of the wearer on the same turn as its owner. The shadow disappear if the enemy is dead or unconscious.

 

[jgsugden]

Scimitar of Speed allows a bonus action attack with no requirement that you use your action to make an attack. This allows you them to attack as a bonus, and then ready an attack to make on another creature's turn (granting them two sneak attacks).

Alternatively, various feats allows you to make attacks on enemies using your reaction. Sentinel is a great source of reaction attacks for a rogue that is pretty much entirely in the DM's control.

The Optional Mark Rules in the DMG open up access to additional opportunity-ish options for extra attacks. Despite relying upon opportunity-ish situations, it is notable in that it is one of the few ways you can get 3 Sneak Attacks in a round.

The most 'competitive' rogue I have seen had a Scimitar of Speed, the Sentinel Feat and ways to stay invisible (effectively) and hidden. He did less damage per round on average than the big weapon fighters, but was far more consistent and was able to solo a few large monsters by surprising the enemy and getting in 4 sneaks before the enemy acted (He did two sneak attack critical hits on the surprise round and then two more sneak attacks on the first round of combat if he went before the enemy... 42d6+28 was about 175 damage at level 12 IIRC. I recall him soloing a few different hill giants, a glabrezu, a large blue dragon and a beholder...

 

[Blue]

Hmm, so he's a melee rogue as well - that really does highlight the classes' squishiness.

What level are they now? Extra attack will outshine SA, btu SA will keep growing. Don't want to make them too powerful.

Does your rogue have problems delivering SA some runds? Becasue a second attack or an attack bonus might go a long way to making that more consistent and upping DPR without the "obvious" second SA.