Help in getting a second sneak attack

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.
Thank you for good questions.

Yes and yes - 5E rules or 3E inspiration I can use to create 5E magic effects.

When I say "optimizing opportunity attacks" I say the player doesn't use those methods. They're on the level of system mastery as I'm sure you'll agree. This player dislikes multiclassing and is happy playing a singleclassed Thief Rogue.

I guess he just expected sneak damage to bring him close to the top.

But compared to my other über-optimized characters making a single attack for maybe 30 points of damage just doesn't cut it. In the first round he's having trouble even getting a sneak attack, and if he makes a miss the second attack chances are he will end up at the bottom.

The Totem Barbarian Champion, the Paladin Warlock, the Fire Dragon Sorcerer, the Monk all reliably do 30 damage each round. Maybe double that when lucky (or going all out).

In contrast the Rogue simply does not have any "overdrive" to gear into. Not from the build angle (no feats, items or class features to focus on damage). Not from the play angle (no "encounter" or "daily" powers that elevate damage output. About the only thing I've seen is Assassinate, and we are in agreement that's dysfunctional in a hack'n'slash campaign where nobody has any patience for subtlety)

In a theoretical infinite adventuring day, sure sneak might look okay. And in a campaign with all options turned off (that is crunch-poor) maybe it automatically does okay.

But I am feeling my player's pain here; getting squeezed the traditional way: not good enough to play with the martials in combat; not useful/flexible enough to claw equal spotlight with the casters.

About his sole schtick that works well is classic thief spot hidden / look for traps stuff.

But since maybe 90% of our build and minmax energies are spent on combat I'm hoping for ideas that allow him a shot at second sneaks in as organic and non-cheesy ways as possible :)
 

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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.
Nobody's interested in sharing the spotlight. This is a fierce competition to be on top.

But you are onto something - any suggestions for 5E or 3E magic items that - crudely put - allows the Rogue to grant himself a Commander's Strike would do the trick.

Assuming this happens off the rogue's turn, since I'm not interested in violating the core premises here (the rule about only one sneak per turn).

This thread is about applying decades of system mastery in finding a solution that appears simpler than it might be :)

For example - I'm looking at something called "Kyton armor" from 3e. Maybe I can create a thingy that makes an attack on somebody else's turn, and allow the Rogue a second sneak attempt that way.

Another idea is to upgrade the parry (allowed by the feat he's got, maybe Defensive Duelist) into a riposte.

That is, using your reaction to make a counterattack on a miss. That should enable sneaking, right?
 

A Keen Rapier.

Nothing like rolling all the d6s at the table every time you get a 15 or above on your d20 to make you feel like you are doing damage.
 

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."
Could I ask you to explain a bit more? Where's the added damage in here? How does replacing a sword sneak attack with cantrips help?

Or am I just blind?
 

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?
You're entirely right it doesn't have to be sneak damage. That just felt like the natural go-to solution.

I am aware Ras Nsi from my module possesses a Flame Tongue, and since that's a longsword (he persuaded me back at level 1 to allow his elf character to treat his elf weaponry as finessable weapons) it should fall into the hands of this character :)

Though he does only do a single attack in a round. +2d6 fire damage would be insanely good in the hands of a fighter with maybe four attacks. But the Sorcerer never Hastes the Rogue - again the synergy simply isn't there (since it is sneak that makes the Rogue good, and if it was possible to "haste sneak" my problem would be solved already)

But +2d6 fire is merely great, not insanely so, in the hands of a single-attack attacker. Just explaining why I'm still having this conversation even though I'm essentially already planning to implement your suggestion :)
 

Could I ask you to explain a bit more? Where's the added damage in here? How does replacing a sword sneak attack with cantrips help?

Or am I just blind?

OK so you cast Booming Blade while wielding a dagger with 16 dex (for example) at level 5.
When you hit your target, you deal 1d8 thunder damage, plus 1d4 for the dagger, plus 3 for your dex, plus 3d6 from your sneak attack. And you even get an additional 2d8 thunder damage if the victim decides they want to move. Mind you, Rogues get Disengage, so a melee enemy can be stuck in a "Damned if I do, damned if I don't" situation regarding following the Rogue around.
 

Scout gets a second sneak Attack, but it's at high level.
Maybe I should clarify we started this campaign before XGE.

Unfortunately 5E does not allow taking a second subclass of the same class. (I guess this player likes to stay singleclassed, but if you could dual two subclasses of the same class - crucially stacking sneak damage dice - I could maybe have sold that to him)

But you say it's high level.

I really dislike the ideas that keep the Rogue class shackled to a very squishy chassis, and the notion that sneak damage is borderline OP, so we better not allow any paths to minmaxing it.

It's not.

I quite like Blizzard's way, where the squishy martial also is the most fearsome martial. To me, there could easily be at least one subclass that double the sneak dice for players that can't/won't minmax but still like to be competitive.

As far as magic items go you can make one to do whatever you want.
I am sorry but that simply is not helpful.

If you want to help, I need you to offer specific suggestions.
 

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.
Now we're talking - this is exactly the kind of whoppingly intricate and specific proposals I was hoping for :)

I really need to read and reread this before replying, though...
 

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...
Nice :)

Good to know in advance (the party is some ways off that Flame Togue yet). It's a luxurious problem to have to choose between a Speed and Fire weapon...

I'll ask him what he took at 8th level, and if he considered taking Sentinel (for its third benefit). I do see how invisibility would benefit that combo immensely (since hiding is painfully difficult if you like melee combat)

PS. I will simply assume you're aware Rogues aren't proficient with Scimitars and that you fixed this (either the Rogue took extra weapon proficiencies or you made it a shortsword of speed or something).
 
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