Help in getting a second sneak attack


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There are a number of feats and multiclass abilities that can synergise with sneak attack. They are just not necessarily obvious in the way that GWM is obvious.

Feats:
Crossbow expert: additional attack with hand crossbow increases the chance of landing a sneak attack;
Martial Adept: Riposte for a reaction sneak attack, Feinting Attack or Trip to set up a sneak attack;
Sentinel;
Elven Accuracy: Increases chance of a critical hit, critical hits double sneak attack dice.

Multiclass:
Anything that get's an extra attack: more attacks means a better chance of landing a sneak attack, and a general DPS increase.
In particular Fighter Champion (critical hits double sneak attack), Battle Master (see martial adept), Samurai (expecially pared with Elven accuracy). Also Monk Shadow, Kensai (because who doesn't want to sneak attack with a battleaxe?).

And Assassin, without doing either. What's not to love about auto crit with sneak attack? Anything that boosts initiative helps here.
 

So let's go through the current list of the various decision points that can raise the Rogue's DPS. Then see mechanically what are the best ways to accomplish it. Due to player choice we are going to avoid Multiclassing, avoid switching to ranged weapons, as well as ignore the rather unhelpful "advice" of "Well, the Rogue does most of their stuff outside of combat, so they should just suck it up!"

Raise Rogue base weapon damage:
- Item to raise the rogue's DEX. Already in the game.
- Magic weapon with additional damage riders, probably easiest to make it a dagger so that it guarantees going to the Rogue. Also already in the game.
- Magic weapons of larger damage dice that have the Finesse property and give proficiency and thus are able to be used for Sneak Attack (for instance Finesse polearms or two-handed weapons).

Increase Sneak Attack frequency:
- Magic item to allow the rogue two SAs per Rogue turn.
- Item or feat that creates more Opportunity Attacks for the rogue, so they can SA off their turn using their Reaction. I personally am working on a dual-wielding dagger fighting style for my next campaign that allows the roguish character to essentially "step into" their enemy's space and attack. But in order for the enemy to attack back the enemy has to step OUT of the space on their turn because they can't bring their weapons to bear, and this allows the roguish character to make an Opportunity Attack. Thus the character gets usually 3 attacks per round (two from dual-wielding, one from the OA that occurs almost every round) and thus why I only allow it for dagger-wielders.

Increase base Sneak Attack damage:
- Magic item or weapon that increases the Rogue's sneak attack dice from d6s to d8s or even d10s.

Increase Sneak Attack potency:
- 'Keen' weapon or item that increases number of Critical Hits occurring via expanded crit range, thereby doubling SA damage more often. Was in the game during 3E.
- Magic weapon or item that increases number of Critical Hits occurring via giving more attacks with Advantage, thereby doubling SA damage.

Maximize Sneak Attack damage:
- Magic item or feat that allows the Rogue to Maximize their SA damage on a hit. Perhaps either via Charges (so only X number of times per day) or via the mechanic that's been brought up before of 'When you Attack with Advantage and if both rolls hit...' you get to Maximize your SA damage dice. Doing something like this would essentially mimic what Paladins usually do, which is to decide to maximize/smite usually when they roll crits, so that the big damage hit is doubled.

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As mentioned above... the only 'canon' rules already in some version of D&D are the standard magic weapons that increase base damage, and the Keen weapons that increase crit range. In both these cases though, you'd have to rely on your players actually giving said weapons to the Rogue rather than another PC claiming it. The easiest method for that would obviously be making them daggers, but even then you might have some of your more opportunistic players do the math and decide moving down to dagger would actually still be beneficial for them and thus screwing over the rogue.

For me personally... since Feats are a viable part of the campaign being run, I'd just homebrew more feats. The 'Cutthroat' style I mentioned above would be one which would could easily do:

Cutthroat - When you wield a dagger in one or both hands or are unarmed, you may move into and remain within a hostile enemy's space. When that occurs:
- You are considered to have half cover and gain a +2 to your AC.
- You may make melee weapon attacks with daggers or unarmed attacks as normal.
- The enemy whose space you are in may not make melee weapon attacks against you while they remain in the same space (unless they also have this feat). Should they leave the space in order to bring their weapons to bear and attack, you may make an Opportunity Attack against them.


If this seems a little much, you can just remove the bonus to AC part of the feat.

Hope these helped!
 
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I haven't seen it mentioned, but I think a major option that is worth exploring is poison. That fits rogues more then any other class and the rules already have everything you need for it. You can use the poisons supplied in the DMG or you can create your own to operate as you see fit. They can do straight damage, or they can inflict conditions such as Blind or Paralyzed. You can even create effects, such as sending the poisoned creature into a rage, attacking the nearest creature each turn. Use spells for inspiration on effects. The nice thing is, poison works best for a rogue since you only get a single application, so it doesn't mesh well with multiattack.

You can give magic items that support poison, such as a dagger sheath that poisons a dagger as a free action each turn, or a quiver that poisons crossbow bolts.

Add to that, hunting for and discovering poisons taken from slain creatures can add a whole new element to exploration, combat and awards. Purchasing rare poisons can be a good money sink.

Others have mentioned the Feat Crossbow Expert, which I think works for a rogue better then just about anyone. It adds an extra bit of damage, 8 or so damage a turn. It provides an additional attack for sneak attack if the main attack misses. It gives flexibility by attacking a ranged attack. Sharpshooter can be taken later for an even more damage increase. And it gives another avenue for magic items.

Lastly, as others mentioned, you can create magic items. Just make sure you gear them toward being better for a rogue. Items that can only be used once a turn excel at this. For example:

Strahd's Fang: Once per turn when you hit a creature with this dagger, you may deal an additional 1d12 necrotic damage. You gain temporary hitpoints equal to half the necrotic damage dealt. Constructs and Undead are immune to this effect.

Donkey Punch: Once per turn when you make an attack, you may fire a bolt of pure force from this magical hand crossbow. Make an ranged attack roll and on a hit, instead of its normal damage, it deals 3d8 Force damage and the creature must make a constitution saving throw or be knocked prone.

I think there are plenty of options to increasing your Rogue's damage without trying to create unique feats or change the rules. I think keeping your sneak attack working the way it is is important. Trying to make it happen multiple times a turn or even round just kinda takes away the whole "sneaking" aspect of it. Keep it as is and it makes those rare natural 20s and getting to roll 14 d6s at once all that more special.
 
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I haven't seen it mentioned, but I think a major option that is worth exploring is poison. ...

I had considered posting a poison option but the issue you might run into then is that it's not class-specific, though Poisoner's Kit proficiency would be needed. What's to keep the Fighter from coating their weapon in Poison? Then all you've done is increase everyone's damage output (at least to Poison-susceptible creatures), which is not what 5e needs.
 

Assassin gains proficiency with poison kits by default. Is there any reason why the errant rogue doesn't seem to have one of the more damage focused subclasses?

And what about race? Kill them off then reincarnate them as an elf or Halfling.
 
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I had considered posting a poison option but the issue you might run into then is that it's not class-specific, though Poisoner's Kit proficiency would be needed. What's to keep the Fighter from coating their weapon in Poison? Then all you've done is increase everyone's damage output (at least to Poison-susceptible creatures), which is not what 5e needs.

I agree, so I suggested some items that would benefit the rogue by applying the poison. As long as you tailor them to support the rogue, it shouldn't be a problem. As soon as you hit with an attack the poison is used up. The poison can have a time associated with it. After being coated on a normal weapon, it dissipates after 10 minutes.

The rogue's weapons can have special grooves that hold the poison. The poison requires a minimum intelligence to apply correctly or you risk poisoning yourself. It might be possible for a fighter to get one use of a poison in the first attack of combat, but not repeated uses through the encounter.
 

Looks like i was a little late for the party, but I noticed in page 3 CapnZapp said you can't use haste to get an extra sneak attack. I don't think that's quite right.

1. Cast haste on rogue
2. Rogue uses the haste action to make a standard attack (SA 1)
3. Rogue uses his standard action to hold based on the trigger of something you know will happen (like the druid moves).
4. Rogue attack with his reaction on the Druid's turn (SA 2).

Hope that makes sense. Another thing that I have seen (which really works better for the ranged rogue) is utilizing poison a lot for their attacks. We had a HotDQ game that included the dagger of venom. This allowed the rogue to poison her attacks. Even a basic poison is pretty useful if you can spam it. It becomes far better if your party has a poisonous familiar. This works "best" for a rogue as envenoming can be a bonus action for a thief.
 

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."

Yoink!
 

I had considered posting a poison option but the issue you might run into then is that it's not class-specific, though Poisoner's Kit proficiency would be needed. What's to keep the Fighter from coating their weapon in Poison? Then all you've done is increase everyone's damage output (at least to Poison-susceptible creatures), which is not what 5e needs.

Thief can use it every round, other classes have to use a standard action to apply it. A Rogue should also be able to buy it easier than the other classes ie from a Thieves or Assassins guild.
 
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