D&D 5E Rogue multiple sneak attack in a round.

Adb0782

Explorer
Hello everyone,
I'm here trying to make a build about a rogue that constantly can deal 2 (or more) sneak attack in a round, as the Sneak Attack rules say it applies no more than once per turn, but there are no limit about how many times it can be applied in a round. Mostly of times it can happen with opportunity attacks, but that's not the only way.
First: I think the Sentinel feat is gold for this kind of build, as it more than double the chances of taking an opportunity attack in a turn other than my own turn. I suppose even Polearm Master RAW works, as it doesn't say that the attack must be done with the Polearm. So, in theory i can just use a quarterstaff in one hand and any finesse weapon in the other hand for get an opportunity attack when an enemy enters my reach, but as a DM i probably wouldn't allow it, as it seem clear that the intention of the rule is the opposite. Anyway, also some subclass open to grow the chances to get opportunity attacks (for every possible Multi Class I'm assuming an half elf or a kobold): the Battle Master have Brace and Riposte for exemple, but Quick Toss it's even more interesting, because the description of the manouver doesn't start with "when you take the attack action" as many other similar abilities do, so i can ready an action and Quick Toss in my turn with a bonus action, dealing possibly 2 sneak attack in a round independently from what enemies do in their turn and 5 use per short rest it's not so bad, also because it gonna add other d6 to damage, but all at the cost of my reaction. Fighter give me also Action Surge that again it's once a day 2 sneak attacks: ready an action and attack with the second action granted from Action Surge. The class give also a fighting style (duelist or supreme technique for another superiority dice) and some heal with second wind + proficiency with martial weapons for eventually use a whip in one hand and a dagger in the other, having enemies leaving my reach at 5 and 10 ft. The build would be Thief 17/Battle Master 3.
This was my first attempt, then i realized that having just 1 or 2 LV with Hexblade can be also interesting and that probably, with a good positioning, sentinel is more than enough for grant a sneak opportunity attack almost every round. The Hexblade would give me 2/3 times a day 19/20 crit and boost to damage against a creature, spellcasting (and this is very important for the Thief, I'll explain later why), proficiency with mid armor and martial weapons + eventually the fact to be SAD if i accept to choose between a whip and normal finesse weapon, but with the few spells and slots I'm gonna have i suppose it's anyway possible to ignore this and leave Cha at 13/14 prioritizing Dex. With spellcasting come my first doubt: Booming Blade yes or not? It don't apply to the whip, as i said it's not mandatory, but for a good use of the spell i would need also Warcaster and I'm not sure there is enough space, as the feats would be:

For the Half Elf: Elven Accuracy and Dex 18 @5, Sentinel @9, Dex 20 @13...whatever after this, probably Alert or Lucky.

For the Kobold: Fey Touched and 18 Cha @5...the same after this. The Kobold must use Cha if i want to get Fey Touched and as he don't qualify for elven accuracy i wouldn't know what else to choose, but anyway it seems don't have space for Warcaster in both cases.

The fact that i get spellcasting from LV 1 is very important anyway, as the Thief can use the "use an object" action as a bonus action and this include scrolls, but if i don't have any spellcaster LV, or anyway any access to any spell list, i don't qualify for use any scroll till Thief 13 and use scrolls as a bonus action i think it's one of the most powerful features this subclass have (for the same reason: probably also with 1 dip with Arcana Cleric this build can work, giving up the whip), together with the fact that from Thief 17 i get till 4 possible sneak attacks in the first round of combat and this is a nice capstone.

If i would choose the Half Elf way, especially the Half Drow, i could also consider to get till Hexblade 3, for 5/7 darkness + devil's sight a day (and Eldricht Mind all time) and a familiar for help to cover and uncover the point where the Darkness will be casted, as my free object interaction is not enough alone, but with a familiar it will work and the familiar can anyway perform the help action when i can't cast Darkness and he can scout out of combat. This would add also some spells and slots and it will make Elven Accuracy more effective, but at the cost of more delay on Rogue stuff.

Finally: which way and which multiclass you would choose? Battle Master? Warlock? Or Arcana Cleric? Just 1 dip? Or some more levels? Do you think this can be worth the multiclass? Thanks everyone.
 

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ECMO3

Hero
Hello everyone,
I'm here trying to make a build about a rogue that constantly can deal 2 (or more) sneak attack in a round, as the Sneak Attack rules say it applies no more than once per turn, but there are no limit about how many times it can be applied in a round. Mostly of times it can happen with opportunity attacks, but that's not the only way.
First: I think the Sentinel feat is gold for this kind of build, as it more than double the chances of taking an opportunity attack in a turn other than my own turn. I suppose even Polearm Master RAW works, as it doesn't say that the attack must be done with the Polearm. So, in theory i can just use a quarterstaff in one hand and any finesse weapon in the other hand for get an opportunity attack when an enemy enters my reach, but as a DM i probably wouldn't allow it, as it seem clear that the intention of the rule is the opposite. Anyway, also some subclass open to grow the chances to get opportunity attacks (for every possible Multi Class I'm assuming an half elf or a kobold): the Battle Master have Brace and Riposte for exemple, but Quick Toss it's even more interesting, because the description of the manouver doesn't start with "when you take the attack action" as many other similar abilities do, so i can ready an action and Quick Toss in my turn with a bonus action, dealing possibly 2 sneak attack in a round independently from what enemies do in their turn and 5 use per short rest it's not so bad, also because it gonna add other d6 to damage, but all at the cost of my reaction. Fighter give me also Action Surge that again it's once a day 2 sneak attacks: ready an action and attack with the second action granted from Action Surge. The class give also a fighting style (duelist or supreme technique for another superiority dice) and some heal with second wind + proficiency with martial weapons for eventually use a whip in one hand and a dagger in the other, having enemies leaving my reach at 5 and 10 ft. The build would be Thief 17/Battle Master 3.
This was my first attempt, then i realized that having just 1 or 2 LV with Hexblade can be also interesting and that probably, with a good positioning, sentinel is more than enough for grant a sneak opportunity attack almost every round. The Hexblade would give me 2/3 times a day 19/20 crit and boost to damage against a creature, spellcasting (and this is very important for the Thief, I'll explain later why), proficiency with mid armor and martial weapons + eventually the fact to be SAD if i accept to choose between a whip and normal finesse weapon, but with the few spells and slots I'm gonna have i suppose it's anyway possible to ignore this and leave Cha at 13/14 prioritizing Dex. With spellcasting come my first doubt: Booming Blade yes or not? It don't apply to the whip, as i said it's not mandatory, but for a good use of the spell i would need also Warcaster and I'm not sure there is enough space, as the feats would be:

For the Half Elf: Elven Accuracy and Dex 18 @5, Sentinel @9, Dex 20 @13...whatever after this, probably Alert or Lucky.

For the Kobold: Fey Touched and 18 Cha @5...the same after this. The Kobold must use Cha if i want to get Fey Touched and as he don't qualify for elven accuracy i wouldn't know what else to choose, but anyway it seems don't have space for Warcaster in both cases.

The fact that i get spellcasting from LV 1 is very important anyway, as the Thief can use the "use an object" action as a bonus action and this include scrolls, but if i don't have any spellcaster LV, or anyway any access to any spell list, i don't qualify for use any scroll till Thief 13 and use scrolls as a bonus action i think it's one of the most powerful features this subclass have (for the same reason: probably also with 1 dip with Arcana Cleric this build can work, giving up the whip), together with the fact that from Thief 17 i get till 4 possible sneak attacks in the first round of combat and this is a nice capstone.

If i would choose the Half Elf way, especially the Half Drow, i could also consider to get till Hexblade 3, for 5/7 darkness + devil's sight a day (and Eldricht Mind all time) and a familiar for help to cover and uncover the point where the Darkness will be casted, as my free object interaction is not enough alone, but with a familiar it will work and the familiar can anyway perform the help action when i can't cast Darkness and he can scout out of combat. This would add also some spells and slots and it will make Elven Accuracy more effective, but at the cost of more delay on Rogue stuff.

Finally: which way and which multiclass you would choose? Battle Master? Warlock? Or Arcana Cleric? Just 1 dip? Or some more levels? Do you think this can be worth the multiclass? Thanks everyone.


I would choose Battlemaster and Quick Toss. You can actually build towards having 6 dice and other maneuvers (esp Brace) by stacking with Martial Adept and the Superior Technique Fighting style.

Play a Varian Human and take the Martial Adept feat at 1st level, then the Superior Technique fighting style, then battlemaster and you can do quick toss 6 times per short rest, which is nearly at will in most campaigns. Cluttering your bonus action will probably be more of a limit than running out of dice. The extra damage from the maneuver dice will also dampen the loss you get from sneak attack because of the multiclass. Finally you can take Brace as a second reaction maneuver option and you have action surge if you miss with your quick toss, still allowing sneak on turn and as a reaction.

If you go this route and get Brace you may also want to consider a whip to extend your reach

You can also get the fighting style with only a 1-level fighter dip and combining with the feat will give you 2 quick-toss maneuvers per short rest. That is not a lot, but you have a lot of other uses for your bonus action too.

I used quick toss a lot on multiclass Rogues. Usually I use it to get sneak attack on my turn while I cast a spell as an action. I am not trying to do it every turn, but I also only usually have 1 dice because I usually get it from the feat.

The only downside to quick toss is it limits you to daggers, which means you need to find several magic ones by level 6 or so.

If your goal is 2 sneak attacks a round I don't see what Kobold, Half Elf or Hexblade are doing for you. To leverage Elven accuracy you are going to want to use your bonus action for something to grant advantage, which means you could not use quick toss and sentinel and PAM are going to be far less reliable for getting the damage off turn. A Half Elf is a great Rogue, especially if you take the high elf spell option and booming blade, but it is not an 2 sneaks per round build.

Same with Kobold, with Kobold you are going to want to use Draconic Cry which is a bonus action and would conflict with quick toss. Like half Elf Kobold gives you a Cantrip option.

Finally I don't see what Hexblade does for this at all. Hexblade's Curse is nice, especially when combined with Elven accuracy, and steady aim or cunning action-hide. But now you are cluttering your bonus action even more.

Fast Hands and the Thief Subclass does allow you to try to use scrolls as a bonus action, but then you are not using your bonus for sneak attack. Also on a low level dip this is not very powerful because only low level spell scrolls are used automatically. You need to make a spellcasting check to use a higher level scroll and your spell casting ability is usually not going to be awesome and even when it is awesome, the scrolls will still often fail and that is before you even get to make an attack roll or force an enemy save. Even with a 20 casting stat, 4th level spell scrolls will fail 40% of the time and it goes up from there.
 

DrJawaPhD

Adventurer
My answer was going to be what you wrote up for Rogue/BattleMaster, since no feats are required to pull off the 2x Sneak Attack. You have so many options to get the 2x sneak attack, a) Quick Toss + Readied Action (automatic but does lose Extra Attack on your readied action), b) between Brace/Riposte there's a high chance of getting a reaction attack, c) always a chance of standard AOO reactions.

Other great options if you can coordinate with party members would be teaming with an Order Cleric or anyone with Dissonant Whispers to get nearly guaranteed extra sneak attacks
 

Adb0782

Explorer
My answer was going to be what you wrote up for Rogue/BattleMaster, since no feats are required to pull off the 2x Sneak Attack. You have so many options to get the 2x sneak attack, a) Quick Toss + Readied Action (automatic but does lose Extra Attack on your readied action), b) between Brace/Riposte there's a high chance of getting a reaction attack, c) always a chance of standard AOO reactions.

Other great options if you can coordinate with party members would be teaming with an Order Cleric or anyone with Dissonant Whispers to get nearly guaranteed extra sneak attacks
I would choose Battlemaster and Quick Toss. You can actually build towards having 6 dice and other maneuvers (esp Brace) by stacking with Martial Adept and the Superior Technique Fighting style.

Play a Varian Human and take the Martial Adept feat at 1st level, then the Superior Technique fighting style, then battlemaster and you can do quick toss 6 times per short rest, which is nearly at will in most campaigns. Cluttering your bonus action will probably be more of a limit than running out of dice. The extra damage from the maneuver dice will also dampen the loss you get from sneak attack because of the multiclass. Finally you can take Brace as a second reaction maneuver option and you have action surge if you miss with your quick toss, still allowing sneak on turn and as a reaction.

If you go this route and get Brace you may also want to consider a whip to extend your reach

You can also get the fighting style with only a 1-level fighter dip and combining with the feat will give you 2 quick-toss maneuvers per short rest. That is not a lot, but you have a lot of other uses for your bonus action too.

I used quick toss a lot on multiclass Rogues. Usually I use it to get sneak attack on my turn while I cast a spell as an action. I am not trying to do it every turn, but I also only usually have 1 dice because I usually get it from the feat.

The only downside to quick toss is it limits you to daggers, which means you need to find several magic ones by level 6 or so.

If your goal is 2 sneak attacks a round I don't see what Kobold, Half Elf or Hexblade are doing for you. To leverage Elven accuracy you are going to want to use your bonus action for something to grant advantage, which means you could not use quick toss and sentinel and PAM are going to be far less reliable for getting the damage off turn. A Half Elf is a great Rogue, especially if you take the high elf spell option and booming blade, but it is not an 2 sneaks per round build.

Same with Kobold, with Kobold you are going to want to use Draconic Cry which is a bonus action and would conflict with quick toss. Like half Elf Kobold gives you a Cantrip option.

Finally I don't see what Hexblade does for this at all. Hexblade's Curse is nice, especially when combined with Elven accuracy, and steady aim or cunning action-hide. But now you are cluttering your bonus action even more.

Fast Hands and the Thief Subclass does allow you to try to use scrolls as a bonus action, but then you are not using your bonus for sneak attack. Also on a low level dip this is not very powerful because only low level spell scrolls are used automatically. You need to make a spellcasting check to use a higher level scroll and your spell casting ability is usually not going to be awesome and even when it is awesome, the scrolls will still often fail and that is before you even get to make an attack roll or force an enemy save. Even with a 20 casting stat, 4th level spell scrolls will fail 40% of the time and it goes up from there.
Thanks for the answer. 😁
I'm agree with you about everything you said about the Battle Master but i don't see any downside in use daggers for Quick Toss, as i can throw daggers if i want and have a Whip in my other hand for get enemies leave my reach at 5 and at 10 feat both for still more chances of a reaction sneak attack, this should take him safe also, but this kind of tactics can limit the use of booming blade a lot, if not totally, but, especially choosing Sentinel, it makes very difficult to reach me.

About elven accuracy, that's exactly why i ended with half drow with Hexblade 3: get
all the proficiencies i need + double crit chances and damage boost (via Hex and the Curse) against a creature in the most important fights of the day, plus spellcasting, that between the combo Darkness + Devil's Sight 5/7 times a day and the familiar i get from the pact, it grants constant advantage for elven accuracy that with the doubled crit chance seem very powerful. The same can be done with the fighter, getting blind fighting style but it's limited to one use a day of the spell, so it's probably not worth to spend the fighting style.

About Sentinel, i was counting a lot on this: if I'm using a whip and a dagger and I'm behind my tank it will be nearly impossible to even attack me: enemy enters my 10 ft reach? Brace and lock him far away from me, enemy attacks my tank? Sentinel grants me again reaction attack and lock him, enemy moves? He leave my reach at 5 AND at 10 feat if i have a whip in one hand and a dagger in the other one. Now, assuming Quick Toss + ready an action will mostly take my bonus action and my reaction too, mostly of time i wouldn't have the possibility to use other manouvers, cunning action, fast hands and also Sentinel, while giving up Quick Toss, or even Battle Master for Sentinel grants me anyway a large amount of opportunity attacks without negate cunning action and fast hands. And so here it comes the Hexblade, my thoughts was "i lost manouvers but, even with only Sentinel and positioning well, i only get to be attacked more than if i wouldn't use Sentinel, because i can't simply play "hit and run", but the feat is kinda able itself to grant an opportunity attack as a reaction in mostly situations and with a Whip locking enemies mean mostly they won't reach me." That said Hexblade 3, more than the crit 19/20 and some more damage that are already nice, give me the possibility to cast warlock spells of 2nd LV with a bonus action even if they normally require an action and without any spell check. So, for exemple, i can cast hold person as a bonus action, crit automatically on my sneak attack + booming Blade with the dagger and still have a reaction sneak attack via sentinel or whatever else with a whip. Also invisibility, Darkness, suggestion, mirror image, are all spells that benefits from a bonus action casting time, even cloud of daggers can be useful if used with a bonus action, more than that, even spells of 3rd LV will miss not that much as i can be SAD with the Warlock, but the fact that you can cast them as a bonus action it's priceless anyway. I'm thinking about Dispel, Hypnotic pattern, summon fey, all with a bonus action while you keep up your full damage from probably double sneak attack in a round.

Going to the races: half elf was choosed indeed for elven accuracy that stack well with sneak attack's dices and also in this case warlock seem to grant advantage without using a bonus action, while the fighter doesn't.

The Kobold was picked for of course packs Tactics that grants advantage near to every attack, which is nice for our sneak attack and, of course, for use Draconic Cry when he don't use scrolls or cunning action (I see Draconic Cry very thematic so i wouldn't just spamm it every time). Also here, i got to warlock because with Quick Toss this would be more difficult to happen.

Of course I'm not sure if all this from warlock for save bonus actions and give him easy advantages it's really worth the loss of quick toss and manouvers , I just writed here what made me think maybe it is.
 
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ECMO3

Hero
You need thrown weapon fighting style to actually be able to draw enough daggers.
Not true. Drawing the dagger is part of the Quick Toss maneuver:

Quick Toss: As a bonus action, you can expend one superiority die and make a ranged attack with a weapon that has the thrown property. You can draw the weapon as part of making this attack. If you hit, add the superiority die to the weapon's damage roll.
 

Zardnaar

Legend
Last time we used it much was late year. Battle Master is the obvious one. How we did it.

1. Haste. Case haste on rogue use its action to attack, ready your action for another one.

2. Order cleric. Cast a spell on the rogue eg bless. Rogue gets an OOA.Mix with tashas feats for more spells including bless (fae touched iirc)

So putting it togather do the whole party.

BM fighter. Tank sword and board.

Order cleric. Support/controller.

Rogue. Striker.

Sorcerer. Striker with side helping of support. Twin haste.

Make the DM cry.
 

ECMO3

Hero
Thanks for the answer. 😁
I'm agree with you about everything you said about the Battle Master but i don't see any downside in use daggers for Quick Toss, as i can throw daggers if i want and have a Whip in my other hand for get enemies leave my reach at 5 and at 10 feat both for still more chances of a reaction sneak attack, this should take him safe also, but this kind of tactics can limit the use of booming blade a lot, if not totally, but, especially choosing Sentinel, it makes very difficult to reach me.

About elven accuracy, that's exactly why i ended with half drow with Hexblade 3: get
all the proficiencies i need + double crit chances and damage boost (via Hex and the Curse) against a creature in the most important fights of the day, plus spellcasting, that between the combo Darkness + Devil's Sight 5/7 times a day and the familiar i get from the pact, it grants constant advantage for elven accuracy that with the doubled crit chance seem very powerful. The same can be done with the fighter, getting blind fighting style but it's limited to one use a day of the spell, so it's probably not worth to spend the fighting style.

About Sentinel, i was counting a lot on this: if I'm using a whip and a dagger and I'm behind my tank it will be nearly impossible to even attack me: enemy enters my 10 ft reach? Brace and lock him far away from me, enemy attacks my tank? Sentinel grants me again reaction attack and lock him, enemy moves? He leave my reach at 5 AND at 10 feat if i have a whip in one hand and a dagger in the other one. Now, assuming Quick Toss + ready an action will mostly take my bonus action and my reaction too, mostly of time i wouldn't have the possibility to use other manouvers, cunning action, fast hands and also Sentinel, while giving up Quick Toss, or even Battle Master for Sentinel grants me anyway a large amount of opportunity attacks without negate cunning action and fast hands. And so here it comes the Hexblade, my thoughts was "i lost manouvers but, even with only Sentinel and positioning well, i only get to be attacked more than if i wouldn't use Sentinel, because i can't simply play "hit and run", but the feat is kinda able itself to grant an opportunity attack as a reaction in mostly situations and with a Whip locking enemies mean mostly they won't reach me." That said Hexblade 3, more than the crit 19/20 and some more damage that are already nice, give me the possibility to cast warlock spells of 2nd LV with a bonus action even if they normally require an action and without any spell check. So, for exemple, i can cast hold person as a bonus action, crit automatically on my sneak attack + booming Blade with the dagger and still have a reaction sneak attack via sentinel or whatever else with a whip. Also invisibility, Darkness, suggestion, mirror image, are all spells that benefits from a bonus action casting time, even cloud of daggers can be useful if used with a bonus action, more than that, even spells of 3rd LV will miss not that much as i can be SAD with the Warlock, but the fact that you can cast them as a bonus action it's priceless anyway. I'm thinking about Dispel, Hypnotic pattern, summon fey, all with a bonus action while you keep up your full damage from probably double sneak attack in a round.

Going to the races: half elf was choosed indeed for elven accuracy that stack well with sneak attack's dices and also in this case warlock seem to grant advantage without using a bonus action, while the fighter doesn't.

The Kobold was picked for of course packs Tactics that grants advantage near to every attack, which is nice for our sneak attack and, of course, for use Draconic Cry when he don't use scrolls or cunning action (I see Draconic Cry very thematic so i wouldn't just spamm it every time). Also here, i got to warlock because with Quick Toss this would be more difficult to happen.

Of course I'm not sure if all this from warlock for save bonus actions and give him easy advantages it's really worth the loss of quick toss and manouvers , I just writed here what made me think maybe it is.

If your campaign is one you can get lots of magic daggers, or at high level lots of good magic daggers then daggers are fine. The issue with relying on thrown weapons though is you need a lot of them if you are going to do it every round. At 8th level you probably want to go into a fight with 8 magic daggers. If finding them won't be a problem in your campaign then this is not an issue.

With the Half Elf Hexblade there is a lot going on here. First Elven accuracy is feat, then you need another one for Sentinel and another for Quick Toss if you want it (or another multiclass). Using Darkness is an action, using Hexblades curse is a bonus action. This is going to cut into the numbers of sneak attacks you make and you are getting less damage per sneak attack. On a 3 level dip you are losing 2d6 every time you successfully sneak attack AND you are trying less sneak attack because you are using your actions and bonus actions for other things. Not saying it is bad, but it is not optimizing sneak attack I don't think.

Also as a Rogue you can get advantage on your turn through steady aim and as a Kobold you can get it both on your turn and on your reaction with Draconic Cry. So you can already cause advantage with other options besides Devil's sight without burning an action. Pack Tactics is on the Legacy Kobold but not the current Kobold. IF your DM lets you use it great.

If you are using Sentinel and attacking from 10 feet away behind your ally, keep in mind the enemy is going to have a +2 cover bonus.
 
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Not true. Drawing the dagger is part of the Quick Toss maneuver:

Quick Toss: As a bonus action, you can expend one superiority die and make a ranged attack with a weapon that has the thrown property. You can draw the weapon as part of making this attack. If you hit, add the superiority die to the weapon's damage roll.
Yeah. I was wrong. Someone already corrected me.
 

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