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Context

Following up on Can Sneak Attack be used when hitting with an improvised weapon?

By RAW:

Not unless you have an ability that allows Sneak Attack with an improvised weapon

Or, at DM's discretion:

Maybe - if it's similar enough to a qualifying weapon

This means I'm entering homebrew terrain when I'll continue allowing improvised weapons – thrown flasks of Holy Water in this case – to trigger Sneak Attack. And that's exactly my plan. My reasoning for doing so is because of my interpretation of Sneak Attack: it's the placement and skill of the wielder that sets circumstances for dealing extra deadly damage, not the weapon wielded.

Party composition, at level 11: minotaur paladin, animated armor eldritch knight/wizard, undead high elf mastermind rogue, undead tabaxi ranger/assassin/warlock, tiefling warlock.

Some other possibly relevant details about the campaign:

  • My world heavily features devils and undead as allies and adversaries.
  • The mastermind is very inquisitive and therefore obtained the holy water from a befriended cleric NPC.
    • In this case it’s flask of holy water, but I’ll make it a general rule to allow Sneak Attack with all improvised weapons. That means this becomes an option for both PC and NPC.
  • The paladin plays more as a frontline fighter than as "holy warrior versus the unholy".

Question

This question is not about whether it's a good idea to allow this mechanic, or whether my interpretation is "right". I'm mostly interested in how it would imbalance the gameplay for the table, and if there's known issues that I should be aware of as a DM. Please support your statements by experience at your own table. Both player and DM perspectives are much appreciated.

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Allowing sneak attack on improvised weapons could be unbalanced

In this situation there are four very distinct groups of improvised weapon that have different answers:

  1. Improvised weapons that resemble finesse weapons (glass bottles, cutlery, fire pokers, etc.)
  2. Improvised weapons that resemble other weapons
  3. Improvised weapons that don't resemble any weapons
  4. Items that require an improvised weapon attack (Holy Water, Vial of Acid, etc.).

An improvised weapon includes any object you can wield in one of two hands, such as broken glass, a table leg, a frying pan, a wagon wheel, or a dead goblin.

The improvised weapon rules gives us a series of example of what counts as an improvised weapon. The damage type for these improvised weapons will be the same as the real weapon they are most similar to. If they are similar enough they can actually be treated as a real weapon of that kind, as given by the following rule.

Often, an improvised weapon is similar to an actual weapon and can be treated as such. For example, a table leg is akin to a club. At the DM's option, character proficient with a weapon can use a similar object as if it were that weapon and use his or her proficiency bonus.

Improvised weapons that resemble finesse weapons

Any improvised weapon that is sufficiently similar to a finesse or ranged weapon can be treated as one. Therefore not only is it balanced to allow sneak attack on these weapons it is officially supported by the rules. These weapons will all deal a physical damage type; piercing, slashing or (rarely) bludgeoning which is a normal limitation of sneak attack.

Improvised weapons that resemble non-finesse weapons

For improvised which resembled larger, non-finesse, weapons allowing sneak attack may be slightly unbalanced. For instance allowing sneak attack on attacks with a tree branch treated as a great-club would allow a multiclassed character to use both sneak attack and great weapon fighting on the damage roll of the attack. Re-rolling 1's and 2's on sneak attack would be extremely strong.

Improvised weapons that don't resemble any weapon

An object that bears no resemblance to a weapon deals 1d4 damage (the DM assigns a damage type appropriate to the object).

In damage terms these truly improvised weapons are the same as daggers other than the fact they lack the finesse property. By RAW you would not be able to sneak attack them, however in damage balance terms there is no issue allowing it. Even with feats to improve improvised weapons these will always be inferior to a simple dagger.

Items that require a improvised weapon attack

From the description of Holy Water we get:

Make a ranged attack against a target creature, treating the holy water as an improvised weapon.

This rule describes how to calculate the attack roll for holy water. Specifically it says to treat the attack as an improvised attack, not treat the holy water as an improvised weapon which resemble a ranged weapon you are proficient with.

Allowing sneak attack on items like this opens the possibility of sneak attack dealing non-physical damage types. As the physical damages types are commonly resisted at higher CRs this would be a bump to the power of the sneak attack feature. Allowing rogues to deal large amounts of radiant damage significantly steps on the toes of clerics and paladins (as per Someone_Evil's answer) and other items (i.e. Alchemists Fire) would allow them to step on the toes of other casters.

As David Coffron points out allowing sneak attack on items that only require an object interaction and not at Attack action is very strong. The thief's fast hands feature would allow sneak attack on a bonus action in addition to on a readied action. Multiple sneak attacks per round is a huge boost to damage output and allowing it so easily would be unbalanced.

Thematically it's wrong

A side note to the balance concerns, thematically sneak attack is 'precision damage'. There is no way to be precise with a splash weapon. I don't even the DM who has to figure out how to narrate sneak attack from a character throwing a table at something.

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  • \$\begingroup\$ Nice and thorough answer, exactly what I was looking for! But also useful for others that moby have a similar Q, therefore I accepted this one. I might restrict the houserule to category 1 and 3, as this table isn't concerned with stepping on each others' toes, so the damage types are not a concern for my table. Narrating the Sneak Attack was rather easy by the way: he threw the bottle at the exact right moment on exactly the right spot; as the shadow demon turned it's head to attack someone else the cleverly hidden mastermind smashed the flask into the eyes of the fiendish creature. ;) \$\endgroup\$ – Vadruk Apr 3 at 6:10
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    \$\begingroup\$ @Vadruk Glad I could be useful. If it works at your table I fully encourage it and I appreciate that you recognize the issue that might occur at other tables. If this ever does cause an issue at your table you should report back here since you are effectively playtesting homebrew. \$\endgroup\$ – linksassin Apr 3 at 6:14
  • \$\begingroup\$ I made some small adjustments regarding typo's and clarity of categories. Feel free to roll it back if you disagree. \$\endgroup\$ – Vadruk Apr 3 at 6:20
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    \$\begingroup\$ Sneak attack from throwing a table at someone? Two words: Jackie Chan. ;) \$\endgroup\$ – nick012000 Apr 3 at 6:38
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    \$\begingroup\$ @Vadruk After thinking about this for a few days I realised there is a fourth category. I added it to the answer. \$\endgroup\$ – linksassin Apr 8 at 3:42
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This wouldn't affect your party, but I'm answering as it could help someone else with a similar query.

This makes the Fast Hands feature very powerful.

The Thief Roguish Archetype has the feature Fast Hands which says:

you can use the bonus action granted by your Cunning Action to ... take the Use an Object action.

Two objects of particular note are acid and alchemist's fire. A thief rogue who can throw two of these in one turn is particularly effective since these items deal markably more damage then a simple weapon (or cancel out an enemy's action to avoid more damage in the case of alchemist's fire). The standard downside to this tactic is you pass up the opportunity to deal Sneak Attack damage.

Usually, a thief rogue employing this tactic will make a weapon attack and then throw the item with their bonus action. This only allows for one chance to hit for Sneak Attack, while you could throw with both your action and your bonus action without sacrificing the chances to Sneak Attack using your proposed rule.

Additionally, the rogue could use a bonus action to throw the item, and then take the Ready action to throw another (or make an attack) with some trigger that would occur on someone else's turn. This would allow for using Sneak Attack twice in one round, while that is usually impossible without some other method of attacking with your reaction (thanks @Chris Starnes in the comments).

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    \$\begingroup\$ If a thief rogue can throw with Fast Hands, they could use it to get Sneak Attack on their turn and then ready an action to attack outside of their turn. Since Sneak Attack is once per turn, not once per round, they could Sneak Attack twice per round. \$\endgroup\$ – Red Orca Apr 2 at 20:25
  • \$\begingroup\$ @ChrisStarnes Very good point. Something I hadn't considered. \$\endgroup\$ – David Coffron Apr 2 at 20:32
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Depends on the opposition they're meeting.

The main thing you are allowing is letting the Rogue deal its damage as radiant (at whatever cost the holy water has to them) which isn't something they normally get to do. So if they are encountering a lot of things with vulnerability to radiant or resistance to non-magical attacks (as is fairly common among fiends and undead), the rogue will do more than they normally would against those. If they aren't encountering such opponents, throwing holy water probably doesn't come up at all.

Another concern is whether allowing rogues to deal significant radiant damage steps on the toes of Paladins or Clerics, who would normally be the ones to deal radiant damage (See Paladin's Divine Smite feature and the guiding bolt spell as examples) and so this house-rule would let rogues steal (hah!) the moments where Paladins and Clerics get to be extra powerful and cool. (This is possibly something you will want to talk to your players, particularly the Paladin, about.)

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  • \$\begingroup\$ Your answer reminds me of a relevant detail in my campaign: devils and undead are heavily featured in this world. Will add it to the Q. \$\endgroup\$ – Vadruk Apr 2 at 9:58
  • \$\begingroup\$ You might want to (slightly) update your answer after my added details. :) \$\endgroup\$ – Vadruk Apr 2 at 10:12
  • \$\begingroup\$ I would argue the holy water (in the example) does sub-dual damage, the normal radiant and then the sneak attack as bludgeoning or something similar. that way it does not step on the Paladin/Clerics feet \$\endgroup\$ – Reed Apr 2 at 14:13
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    \$\begingroup\$ @Reed that would require and additional house rule, which would a require additional DM fiat for any improvised weapon (used by a rogue). \$\endgroup\$ – Someone_Evil Apr 2 at 14:34
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I don't think it would unbalance the game, because it's A) fairly costly for the damage it does, B) has quite limited range, and C) already requires an action to throw just one, so can't benefit from multiple attacks or "being used as an item".

Honestly it seems like a cool idea, and it rewards player creativity. Unless they're all level 1 and they have a hundred vials of holy water, 2d6 damage isn't a crazy amount, especially given the other limitations. (Also, I assume this is being used by the undead mastermind rogue? Carrying a bunch of fragile vials of holy water, as an undead? That has the potential to go VERY wrong if they trip...)

Edit, due to complaints about the answer only dealing with Holy Water:

Improvised Weapon, according to RAW, leaves it up to the DM to set the damage die and type for the object in question, as well as determining if it is close enough to an actual weapon to be counted as such. If not, they don't get their Proficiency Bonus to the attack roll. So, normal weapons will in most cases still be better. I find it hard to imagine scenarios where it could be badly abused, if the DM is making reasonable calls on what can be used. (Also, it's fun and thematic!)

Regarding fears that the Rogue Fast Hands ability will significantly unbalance the game, I don't see that being the case. You can only do Sneak Attack damage once per round anyway. Further, it's dependent on having Advantage on the Attack Roll, which further limits their options.

Conversely, if you want an excuse to disallow it, it could be argued that Holy Water is magical, and thus subject to the rule on DMG p.141:

If an item requires an action to activate, that action isn't a function of the Use an Object action, so a feature such as the rogue's Fast Hands can't be used to activate the item.

Further, I would also argue that throwing a splash attack into someone's face could very reasonably be considered a precision attack.

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    \$\begingroup\$ This answer only deals with Holy Water, the OP asked for "all improvised weapons" can you expand on it? \$\endgroup\$ – linksassin Apr 3 at 0:14
  • \$\begingroup\$ Welcome to RPG.SE! Take the tour if you haven't already, and check out the help center for more guidance. \$\endgroup\$ – V2Blast Apr 3 at 1:18
  • \$\begingroup\$ @linksassin Sure; Improvised Weapon, according to RAW, leaves it up to the DM to set the damage die and type for the object in question, as well as determining if it is close enough to an actual weapon to be counted as such. If not, they don't get their Proficiency Bonus to the attack roll. So, normal weapons will in most cases still be better. I find it hard to imagine scenarios where it could be badly abused, if the DM is making reasonable calls on what can be used. (Also, it's fun and thematic!) \$\endgroup\$ – ColdComfort Apr 3 at 9:04
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    \$\begingroup\$ You should edit that information into your answer to make it more complete. For the record I disagree that it is balanced see my answer for reasoning but answering the whole question should get you some upvotes. \$\endgroup\$ – linksassin Apr 3 at 10:45
  • \$\begingroup\$ "You can only do Sneak Attack damage once per round anyway." this is incorrect, you can deal sneak attack once per turn. You can get sneak attack on your reaction. You also get it from an adjacent ally so don't always need advantage, \$\endgroup\$ – linksassin Apr 8 at 5:30
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Don't forget about longer term. Allowing them to use holy water this way establishes the precedent that in your world rogues can use Sneak Attack while throwing vials at enemies. If they can Sneak Attack with vials of holy water then they can also Sneak Attack with vials of acid, vials of poisons/toxins, flasks of oil, etc. If you don't want to allow this in the future then you need to establish up front that it only applies to holy water and you should probably try to include some sort of explanation for why this is the case.

Players may also try to expand the ruling by saying that if it applies to throwing vials then it should apply to other thrown items as well. "If a Sneak Attack allows me to throw a vial at a vulnerable spot that does more damage then it should also allow me to throw x at a vulnerable spot that does more damage..." And they will be making a valid point. Logically a bonus with one thrown item should also apply to most other thrown items.

The solution that I have been using and seems okay so far is to hold a strict definition of the Sneak Attack as defined in the PHB.

Then to handle cases like the holy water vials I give a bonus for making a sneaky attack even though it isn't a Sneak Attack. If the rogue has advantage and the rogue's attack is coming from an unexpected direction then I will give bonus damage as if it were a Sneak Attack, but capped at 3d6 unless they really come up with something special. This way they have some incentive and ability to be creative and be unconventional especially at lower levels but things don't get out of hand. The part about hitting from an unexpected direction limits this to only one or maybe two hits per creature. Even if they don't know the location of the rogue, knowing the general direction the first attack came from means that any future attacks from that area cannot be an unexpected direction.

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    \$\begingroup\$ I don't really understand your answer. It seems like you are saying that this imbalances the game but you don't actually come out and say that. \$\endgroup\$ – NautArch Apr 2 at 15:07
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    \$\begingroup\$ Maybe you answered this before I edited those details into the question, but as I state in the Q: the plan is already to allow all improvised weapons to follow this rule and I have a reasoning for it ready (see Q). That results in making the first two paragraphs redundant as they are now. So I think this answer could improve if you remove/rephrase those. What comes after, regarding the "sneaky attack", is a good tip! \$\endgroup\$ – Vadruk Apr 2 at 19:59
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My experience as a rogue player. My DM has allowed players to upgrade arrows with vials of holy water, alchemist fire, and also herbicides. Because the vials are then considered a part of a ranged weapon attack they are qualify for sneak attack. The holy arrows only add 1d6 damage to fiend/undead as the amount of holy water is reduced to allow the arrow to fly. The cost for the holy water arrows in our campaign is 50 gold per arrow.

To be honest I cannot tell you if adding an average of 3 damage per round is really making much of a difference, but grabbing that extra d6 and telling the DM what kind of arrow I am using is really fun. Also on a miss a single tear goes down my rogues face as he watches 50 gold or more smash into a wall. (Herbicide arrows 1d8 are 100g per arrow.) In my experience, it isn’t unbalanced; it’s fun.

Back to your group, it looks like the Tavern Brawler feat will be almost mandatory for the rogue to keep up with enemies' increased AC.

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    \$\begingroup\$ Most of your answer describes your experience with the premise, but you don't really go into detail on the outcome. You say you don't think it's affecting the balance of the game, but you don't really go into detail. I think the answer would be improved if you elaborated on how that house-rule/homebrew has affected the game in more detail. \$\endgroup\$ – V2Blast Apr 8 at 4:50
  • \$\begingroup\$ Do the sneak attack damage on a holy arrow deal piercing or radiant damage? That significantly changes how strong this is. Also adding vial/enchanting weapons isn't a homebrew rule on improvised weapons pre-se. Though this is still useful insight to the question. \$\endgroup\$ – linksassin Apr 8 at 5:27
  • \$\begingroup\$ Piercing damage for sneak attack \$\endgroup\$ – Alk Apr 8 at 5:29

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