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I would like to break the stereotype that rogues are always super stealthy sneaky types that appear from the shadows and strike and then disappear, for me that makes the flavor of the game not as fun and reduces the amount of decision making in-game. This is the reason I haven't considered playing rogue ever.

I am selecting the thief rogue archetype in order to be able to take advantage of the use an object bonus action, and combine it with free actions for maximum effectiveness to allow for stunting and debuffing to gain the advantage required for sneak attacks. Is this a mechanically sound way to reliably trigger sneak attacks?

Ways this could potentially be implemented in practice:

  • Throwing dust into the eyes of an enemy
  • Using tinderbox to light their clothing, hair, or fur on fire
  • Using ten foot pole or quarter staff to poke and harass them
  • Using ropes and whips to attempt to trip them up or lasso them
  • Throwing caltrops, ball bearings, or oil, under their feet
  • Pantsing them or messing with their clothing in a similar way
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    \$\begingroup\$ Comments are not for extended discussion; the conversation about pantsing beholders has been moved to chat. \$\endgroup\$ – Someone_Evil Jul 7 at 13:34
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TL/DR: No go. You're asking for the benefits of other rogue subclasses and of higher level abilities.

No, it is not mechanically sound.

The hit-and-fade rogue combat style doesn't require any special DM adjudication. The rules are fairly solid on Hiding: Cunning Action lets you Hide as a bonus action, being Hidden grants advantage, and advantage enables Sneak Attack.

Few of your suggestions have any rule support, and the ones that do actually don't support working with the Thief Rogue as a bonus action via Fast Hands.

  • Throwing Dust - No mechanical support.
  • Igniting Clothes - No mechanical support.
  • Poke & Harass - Negative support. This is the Help action; Mastermind Rogues can explicitly do it as a bonus action, not Thief Rogues. Using a ten foot pole is not an option either, using Help without being adjacent is also a feature of the Mastermind Rogue.
  • Trip - Negative support. This is either a Battlemaster Fighter maneuver (Tripping Attack) or a Way of the Open Hand Monk ability (Open Hand Technique), both of which require use of a limited resource. They're also only truly of benefit to the tripping character if it has more than one attack in a round - a rogue with the Martial Adept feat using two weapons could pull it off.
  • Throwables - Mostly negative support.
    • Caltrops have rules for inflicting damage and affecting movement, they don't grant advantage. They can be deployed with Fast Hands.
    • Grease is a first level spell - with an opportunity cost to learn it and a resource cost to use it.
    • Ball Bearings have rules that can knock somebody prone (which would grant advantage), and Fast Hands would let you deploy them as a bonus action. However, they're a weak choice: DC 10 is very easy to make, they can be ignored by moving slowly, and because the save is triggered on movement, it happens on the enemy's turn, not the rogue's, and the enemy could just get up again. To make an attack while the target was prone, the rogue would have to use their Bonus Action to deploy the ball bearings, the Ready action to wait for the prone, and save their Reaction to make the attack. It's expensive in terms of action economy, and hinges on an easy-to-make or easy-to-ignore saving throw, which means there's a high chance the whole turn will be wasted.
  • Messing with Clothing - Negative support. This is the Help action; see above.

The Thief Rogue's Fast Hands is primarily meant to make them a fast lock picker and fast pickpocket, not an additional way to grant combat advantage.

  • Granting advantage to another as a Bonus Action is the province of the Mastermind Rogue via Master of Tactics; granting advantage to oneself is clearly a more powerful ability.
  • Getting Sneak Attack without a nearby ally and without Hiding is the province of the Swashbuckler Rogue via Rakish Audacity.
  • The Inquisitive Rogue via Insightful Fighting can single out one person for Sneak Attack (but not advantage) with an opposed skill check.

Giving yourself advantage as Bonus Action is a level 13 feature of the Arcane Trickster Rogue via Versatile Trickster. Even then, it has setup restrictions - it requires having Mage Hand pre-cast and in a proper position. This is the same level a Thief Rogue gets the ability to use any magic item in the game via Use Magic Device, a very potent ability. Adding a setup-free version of an L13 ability from a different subclass to the Thief Rogue at L3 is clearly unbalanced.

The other classes that get advantage without Hiding have to expend resources for it. You're either asking the DM to create rules from whole cloth, or you're trying to claim a different and cheaper route to the abilities of a different class or subclass.

Interacting With Objects is generally for affecting the environment, not affecting other creatures directly - opening doors, throwing levers, etc. You're not going to gain advantage this way without that same level of DM buy-in. Even then, it's nothing specific to your character build - if the DM has put something in the environment that affect other creatures and somehow grant advantage, it should work just as well for any other character.

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    \$\begingroup\$ The UA class feature variant "Cunning Action: Aim" might also be relevant here, although I suspect it lacks the desired flavor for what the OP is looking for -- it's difficult to justify how standing in place would have anything to do with distracting pranks against the target. But if nothing else, it's a mechanic for a low-level rogue to grant themself advantage on one attack. \$\endgroup\$ – Ryan C. Thompson Jul 6 at 16:41
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    \$\begingroup\$ @RyanC.Thompson I prefer to avoid discussing playtest content until it's actually released in a finished form. \$\endgroup\$ – T.J.L. Jul 6 at 19:11
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    \$\begingroup\$ I'd say throwing dust or lighting somebody's clothes on fire would be colorful descriptions for the Help action, i.e. to grant an ally advantage on an attack. It still wouldn't be anything you can do with Cunning Action (Mastermind aside) and you can't Help yourself, only an ally, so I don't think it really changes anything in the answer. \$\endgroup\$ – Darth Pseudonym Jul 6 at 19:12
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    \$\begingroup\$ "there's a high chance the whole turn will be wasted." That's true of the same strategy in real life. (Imagine Home Alone 5, with two competent adults as intruders... a very dull movie.) \$\endgroup\$ – jpaugh Jul 6 at 21:18
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    \$\begingroup\$ BTW, the paragraph that begins "The other classes that get advantage without Hiding have to expend resources for it. " is a very good TLDR, and would work well as the first paragraph, removing the need for a TLDR. \$\endgroup\$ – jpaugh Jul 6 at 21:23
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Your approach isn't supported by the rules-as-written. If you want a rules-supported way to do this, you could re-flavour the Swashbuckler subclass or take the Martial Adept feat.

Swashbuckler

While Swashbuckler won't give you advantage, it will enable you to sneak attack in melee without allies nearby - as long as no other creatures are next to you.
That might require some maneuvring to pull off, and feels to me like it fits the flavour here pretty well. Also, higher level swashbucklers with expertise in Athletics can be pretty good at grapple/shove, which isn't super useful by itself but does fit the flavour pretty well if you can find something to synergize with it.

Take the feat: Martial Adept

Martial Adept (or three multiclass levels of Fighter(Battle Master)) gives you maneuvers. One of the maneuvers that fits your objective is Feinting Attack: this lets you use a bonus action to gain advantage (and extra damage) on your next attack. This fits both the flavour and mechanics you're looking for, at the cost of a feat, or three levels in another class. It is a limited use resource (recharging on a short rest), but it gets you more attacks with advantage.

Martial Adept (PHB, Ch 6)
2. You gain one superiority die, which is a d6 (this die is added to any superiority dice you have from another source) This die is used to fuel your maneuvers. A superiority die is expended when you use it.
3. You regain your expended superiority dice when you finish a short or long rest.

If you mutliclass into Battle Master, you'll get more dice and more maneuvers, but that's a steeper cost than the feat.

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What you need here is a homebrew, rather than trying to change existing mechanics

Rather than answering the specifics of your question, I am hoping that I am answering more to the intent. You basically don't like the idea of always hiding behind things, but you want to be able to get the mechanical advantages (not to be confused with the advantage mechanic) of being able to hide / being hidden.

I can definitely see a homebrew which can balance this, but answers here have to be backed with experience so I can't really suggest one. The best I can do is give you a list of things to think about, and suggest you create a homebrew rule, then post it as a question here.

Things to think about:

  1. How what you do benefits the rogue only, and can only be done by the rogue (IE: What is to stop anyone throwing sand)?
  2. How do you balance a mechanic seemingly aimed at one creature (throwing sand) vs a mechanic that affects every creature (ie: being hidden from everyone)?
  3. How do you not step on the toes of other classes and features (such as tripping people over)?
  4. How would this ability interact with cunning action as it stands?

Potential answers as a start for a homebrew power / rule:

  1. Rather than try and allow the rogue to use existing items or features to gain a benefit, make it part of cunning action that you can (for example) 'gain the benefits of being hidden by causing a distraction, to see how successful roll a check of some kind contested by the creatures passive perception'
  2. This is going to be tricky, you might simply have to accept the feature not being as powerful as being hidden, you simply can't expect a standard distraction to distract everyone. The flip side, is that you can probably use this feature even in an open field where there are no places to hide, so your DM has leeway to play around with it.
  3. I would keep this as giving the benefits of the hidden condition vs a single enemy and not try to add new features
  4. I would probably remove the ability to hide as a bonus action; so you can only dash, disengage or use this new ability as a bonus action.

Final thoughts

I think it is quite possible to balance this kind of feature against hiding, the exact wording of such a power may be difficult to arrive at. If you are the type that is going to look for how to abuse edge cases I would advise against modifying any features at all, but if you and your DM work sensibly together this could be workable.

IE:

You can cause a distraction which prevents one creature from being aware of your location until [whatever conditions normally end hidden aside from just looking in your direction]. As a bonus action you can perform a Dexterity (Stealth) check contested by the targets passive perception. On a success you gain the benefits of the hidden condition against that creature, on a failure you do not. You can describe this distraction however you wish, but gain no additional mechanical benefits beyond remaining hidden. Creatures with blindsight, tremor sense or other special senses may be immune to this ability.

As a player you would likely have to accept it not being quite as powerful in some (most?) situations, but to be honest this seems pretty fun regardless :)

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  • \$\begingroup\$ I think there's still a balance issue with this whole approach. Hiding in general requires that you have something to hide behind as the limiting factor. Removing this is extremely significant. Rangers get Hide In Plain Sight at level 10 (and still require some terrain). You're giving a (limited) form of permanent invisibility; I feel like this should have finite uses per short/long rest. \$\endgroup\$ – Andrzej Doyle Jul 7 at 9:08
  • \$\begingroup\$ @andrzej doyle that is partly why I don't suggest allowing them to actually hide, and certainly not from more than one creature (hide in plain sight makes you properly hidden from everything, that's a huge difference). But really if there isn't enough to hide behind in any given combat then the DM is doing it deliberately. But you are right, balance issues need to be looked at. \$\endgroup\$ – SeriousBri Jul 7 at 9:39
  • \$\begingroup\$ Arguably they are "actually hiding" from that one creature (they "gain the benefits of being hidden"). And apart from infiltration purposes, being hidden from one creature (i.e. the one you're going to attack, or the one you're going to move past without provoking) is often just as good as being hidden from all. Simply giving advantage on attacks, without being hidden, would reduce the potential issues (though as per the top answer I still think that even this alone is mechanically unbalanced). \$\endgroup\$ – Andrzej Doyle Jul 8 at 15:49
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While a DM could easily let you use a bonus action handful of sand to grant advantage on your next attack, it's not supported by the RAW. I think most DMs would be receptive to this, but you'd need to discuss this with them first. Using sleight of hand to pants your opponent, or set their clothes on fire is within the realm of things you could do with your bonus action, but would require your DM's buy-in.

The ball bearings can knock opponent's prone to grant advantage, but that requires your opponents to move over half their speed on the previous turn, through the ball bearing field and fail a dex save.

The most mechanically similar option would be the Inquisitive Rogue instead. They can use their bonus action to allow their sneak attack on an opponent, if they can succeed on a contested Insight vs Deception check. While this is supposed to be from watching your opponent's moves, you could flavour it as you causing a distraction.

Other options are being a swashbuckler, who gets to use sneak attack on an opponent if you aren't within 5' of any other opponents. You don't need to make a roll for this, but you could also flavour that as dirty tricks like throwing sand in the face.

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Yes, absolutely mechanically sound

The rules for advantage state, in part:

The GM can also decide that circumstances influence a roll in one direction or the other and grant advantage or impose disadvantage as a result.

How often this comes up will depend on your DM, but considering that it is also advised to give advantage/disadvantage of numerical bonuses whenever the environment is used to favor a creature or circumstances are manipulated to favor a combatant (beyond what is inherent to them, c.f. DMG 239), it is entirely reasonable to try and consistently gain advantage via clever play rather than via stealth. How effective this will be will depend on your ability to correctly guess what your DM thinks is sufficient to grant advantage and not terribly difficult to bring about. Your specific suggestions strike me as mostly problematic on account of their not being 'use an object' actions, and for several they also fail to change the circumstances of the combat, but in general the idea of using Use an Object actions to cause problems for your enemies is not terrible, though you certainly can't rely on any universally-applicable cross-game technique.

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To add to the other answers here, in fifth edition hiding is not the primary way a rogue is expected to qualify for a sneak attack. From the Basic Rules:

Beginning at 1st level, you know how to strike subtly and exploit a foe’s distraction. Once per turn, you can deal an extra 1d6 damage to one creature you hit with an attack if you have advantage on the attack roll. The attack must use a finesse or a ranged weapon.

You don’t need advantage on the attack roll if another enemy of the target is within 5 feet of it, that enemy isn’t incapacitated, and you don’t have disadvantage on the attack roll.

While being hidden does offer an attacker advantage, it’s far from the only way, and hardly reliable since even with Cunning Action it’s not often easy to successfully hide in the middle of a fight. If you intend to be in melee, as long as you are not fighting one-on-one, you are likely to be able to sneak attack anyway.

If you are wanting to fight one-on-one, I agree that the swashbuckler suits the way you want to describe your character’s actions better than the thief. It augments your sneak attack so that:

you don’t need advantage on the attack roll to use your Sneak Attack against a creature if you are within 5 feet of it, no other creatures are within 5 feet of you, and you don’t have disadvantage on the attack roll.

What you are narrating and flavouring here isn’t necessarily gaining advantage, but how you are exploiting the “foe’s distraction” - whether you have advantage or not. Rather than looking for additional ways to get advantage or sneak attack that aren’t in the rules, I’d recommend choosing swashbuckler and describing the flourishes like the pinch of sand etc as what it looks like when your character sneak attacks - they obviously learned to fight dirty!

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While I agree with T.J.L's answer, when it comes to the point of not getting something for free when it'd otherwise cost class features etc, I feel that a simple reflavouring of stealth will achieve most of what you want.

The rules are fairly solid on Hiding: Cunning Action lets you Hide as a bonus action, being Hidden grants advantage, and advantage enables Sneak Attack.

You just don't want to flavour the bonus as hiding. No problem - just follow the rules for hiding when it comes to mechanics and just narrate it differently.

It basically boils down to the DM deciding that hiding makes sense and passing a dex(stealth) check vs wisdom(perception). Instead, let the DM decide that trying one of the distractions makes sense and maybe tweak the checks required (perception still makes sense or perhaps insight, while stealth is a bit harder to justify but I don't see why changing it to sleight of hand would be imbalancing). Note that for the latter, it'd need to substitude the stealth option entirely, ie you can't gain advantage both ways.

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    \$\begingroup\$ Some of the ideas presented by OP are situations that they wouldn't normally be able to Hide. Are you suggesting not just a reflavoring, but allowing the Hide action at times/places when they normally couldn't? \$\endgroup\$ – NautArch Jul 7 at 17:05
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Unless an item specifically allows it, you would not be able to use a bonus action to get advantage in this way.

While T.J.L.'s answer is excellent for showing what balance implications there are for a DM allowing 'Use an Object' to be used in that way, and Peter Chaplin gives excellent alternatives, I believe it's useful to walk through why these actions would not be covered by 'Use an Object'. I hope it can give you inspiration on what a Thief Rogue can do, and hopefully temper any feeling that you personally might be limited by the capabilities of other classes/archetypes.

'Use an Object' has multiple jobs. I'll let the PHB take it from here and then break it down (numbering is mine):

(1) You normally interact with an object while doing something else, such as when you draw a sword as part of an attack. (2) When an object requires your action for its use, you take the Use an Object action. (3) This action is also useful when you want to interact with more than one object on your turn.

So in summary, the 'Use an Object' action is:

  1. Barring #2, Not needed to interact with an Object when it's used as part of another action.
  2. The Action requirement of using Objects that explicitly need an Action to use
  3. The Action taken for interacting with an Object

The key takeaway is that unless an object explicitly has wording saying you can use it "as an action" (2) 'Use an Object' is for doing something to the object (3), not use the object to do something (1).

Looking at the suggestions

Throwing dust into the eyes of an enemy

Picking up the dust could be 'Use an Action'. Dust is not a defined object with an "as an action" clause, and you're trying to use the dust to do something (blind), not do something to the dust, so 'Use an Action' would not be applicable when throwing it.

Using tinderbox to light their clothing, hair, or fur on fire

The rules for Tinderboxes say lighting something "with abundant, exposed fuel--takes an action", with anything else taking a minute. Whether clothing, hair, or fur can be considered abundant and exposed fuel, is up to your GM. If it is, then you could light it with 'Use an Object'.

Using ten foot pole or quarter staff to poke and harass them

Neither item has an "as an action" clause, and it is trying to use the pole to do something rather than do something to the pole. Depending on intent, this would be a Help, Attack, or Improvised Action.

Using ropes and whips to attempt to trip them up or lasso them

As above, Ropes don't have an 'As an Action' clause and you are using the rope to do something, not do something to the rope. This would be either Help or Improvised Action depending on intent.

Throwing caltrops, ball bearings, or oil, under their feet

All three of these items have an 'As an Action' clause, so this would be fine.

Pantsing them or messing with their clothing in a similar way

This one is debatable and up to the GM.

tl;dr

'Use an Action' is for explicitly mentioned item usage, or doing things to objects. Of the strategies you mentioned, only the Ball Bearings and maybe the Oil could be used as a bonus action by a lvl 3 Thief Rogue in order to potentially get advantage. You could still do all of these things as other actions, though. You could do it to help your team, or maybe they'll be disadvantaged long enough to last into your next turn and you'll have advantage at that point. It's not that they can't be done, only that it can't be done as a Bonus Action using Fast Hands.

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