Aericsteele’s D&D 5e RPG Main Thread SRD

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One of the primary roles of a Dungeon Master, in my opinion, is to interpret rules and make determinations regarding how and when rules should apply to any given situation in the game. Reasonableness is the biggest factor in making these determinations Some rules are relatively black and white and require little in the way of interpretation or modifications, while other rules are a little more ambiguous or cannot be reasonably applied as written without some form of interpretation being made as to how, or even if, they apply in a given situation.

Rogues Use of Sneak Attack: The Players Handbook states that for a rogue to use their sneak attack bonus for damage on a foe, the target need only be adjacent to someone or something hostile to that target. The rule is adjusted as follows:

Sneak attack damage is applied when there is reasonable grounds to determine that the rogues target is sufficiently distracted and/or unaware of the rogue's attack. Attacks that occur at the targets flanks or rear apply this damage bonus, as would any attack ranged or otherwise that is made when the rogue is hidden. The damage bonus does not apply, however, to a target that is actively engaged with the rogue, or obviously aware of the rogue's presence regardless of whether or not there is a creature hostile to target that happens to be adjacent to the target unless that creature has performed some action that would distract the target such as having attacked the target during the hostile creatures turn or having taunted or made some active move to distract the rogue's target.

Rogues Cunning Action Ability:

This ability cannot be utilized in a manner that would provide the player with what would essentially be an unlimited amount of advantages on attack rolls and sneak attack bonuses each round. In general a player can only use one bonus action per round which effectively prevents the player of a rogue character from attacking from the shadows, using a bonus action to disengage, and then use another bonus action to hide because you cannot use two bonus actions in one round.

The issue of ranged attacks then arises as the question becomes if the character is hidden can they use an attack action followed by the hide action as their bonus action. The answer is yes, but they would not be able to simply redo this process every round and expect to have an advantage on their attack rolls every round. The reason they would not gain an advantage is that, after that initial attack, the enemy is aware of their presence and location. While the rogue may be "hidden" insofar as the enemy cannot see them, and thus any attack made against the rogue would be at disadvantage, it would not be reasonable to believe that they have the advantage of surprise the enemy knows now that they are being attacked and that they are being attacked from a particular direction.

The only way to really maintain this pattern would be if the character was to be hidden, then made a ranged attack, used bonus action to hide again and then used a move action to move to a different location. However, the target would be allowed to make a perception check when the character moved and if at any point during that movement the character was no longer obscured, the perception check would be made with advantage.
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