Mistwell
Crusty Old Meatwad
I am about to play a Halfling Rogue (9th level, Arcana trickster) / Sorcerer (3rd level, Draconic or Wild). He is attuned to a Dagger of Blindsight, and has the spells Fog Cloud, Minor Illusion, and Tasha's Hideous Laughter (in addition to many others).
I have a lot of questions about how to adjudicate the Hide action and its interactions with some other abilities.
Potentially relevant rules:
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Strategy: On the Rogue's turn they will move to a Spot, cunning action hide as a bonus action, and attempt to cast an upcast 3rd level Tasha's Hideous Laughter spell on as many foes they can see up to a maximum of three foes, with the intent to use Magical Ambush to impose Disadvantage on the initial saving throw against Tasha's Hideous Laughter (but not on any following saving throws that creature makes as it will not be made on the same turn).
The Spot they move to will change the scenario each time. It might be an existing Fog Cloud spell (which they can see through because of their Dagger of Blindsight), an existing Minor Illusion spell with two walls (cast on a prior round), behind an ally at least one size larger than them (trying to use naturally stealthy), or it might be behind a cart large enough to provide some meaningful cover against foes (halfling is 5 feet tall, cart is at least 4'2" feet tall), or the corner of a building.
How would you resolve this strategy for each foe in each of these depicted scenarios which each lists a different Spot:
Scenario 1: The Cart, halfling PC is #4, foes are 1, 2 and 3, 5 is just an ally
Scenario 2: The Ally, halfling PC is #4, Ally is #5, foes are 1 and 2
Scenario 3: The Fog Cloud
Scenario 4: The Illusion, minor illusion is the red wall next to PC
Scenario 5: The Corner.
I have a lot of questions about how to adjudicate the Hide action and its interactions with some other abilities.
Potentially relevant rules:
Line of Sight: To determine whether there is line of sight between two spaces, pick a corner of one space and trace an imaginary line from that corner to any part of another space. If you can trace a line that doesn’t pass through or touch an object or effect that blocks vision—such as a stone wall, a thick curtain, or a dense cloud of fog—then there is line of sight.
Cover: The accompanying diagrams illustrate cover on squares or hexes. To determine whether a target has cover against an attack or other effect, choose a corner of the attacker’s space or the point of origin of an area of effect. Then trace imaginary lines from that corner to every corner of any one square the target occupies. If one or two of those lines are blocked by an obstacle (including a creature), the target has Half Cover. If three or four of those lines are blocked but the attack or effect can still reach the target (such as when the target is behind an arrow slit), the target has Three-Quarters Cover.
Naturally Stealthy (Halfling trait): You can take the Hide action even when you are obscured only by a creature that is at least one size larger than you.
Cunning Action (Rogue Class Feature at level 2): Your quick thinking and agility allow you to move and act quickly. On your turn, you can take one of the following actions as a Bonus Action: Dash, Disengage, or Hide.
Magical Ambush (Rogue Subclass Feature at level 9): If you have the Invisible condition when you cast a spell on a creature, it has Disadvantage on any saving throw it makes against the spell on the same turn.
Hide [Action]: With the Hide action, you try to conceal yourself. To do so, you must succeed on a DC 15 Dexterity (Stealth) check while you’re Heavily Obscured or behind Three-Quarters Cover or Total Cover, and you must be out of any enemy’s line of sight; if you can see a creature, you can discern whether it can see you. On a successful check, you have the Invisible condition. Make note of your check’s total, which is the DC for a creature to find you with a Wisdom (Perception) check. The condition ends on you immediately after any of the following occurs: you make a sound louder than a whisper, an enemy finds you, you make an attack roll, or you cast a spell with a Verbal component.
Invisible [Condition]: While you have the Invisible condition, you experience the following effects. Surprise. If you’re Invisible when you roll Initiative, you have Advantage on the roll. Concealed. You aren’t affected by any effect that requires its target to be seen unless the effect’s creator can somehow see you. Any equipment you are wearing or carrying is also concealed. Attacks Affected. Attack rolls against you have Disadvantage, and your attack rolls have Advantage. If a creature can somehow see you, you don’t gain this benefit against that creature.
Heavily Obscured: You have the Blinded condition while trying to see something in a Heavily Obscured space. See also “Blinded,” “Darkness,” and chapter 1 (“Exploration”).
Blinded [Condition]: While you have the Blinded condition, you experience the following effects. You can’t see and automatically fail any ability check that requires sight. Attack rolls against you have Advantage, and your attack rolls have Disadvantage.
Cover: Cover provides a degree of protection to a target behind it. There are three degrees of cover, each of which provides a different benefit to a target: Half Cover (+2 bonus to AC and Dexterity saving throws), Three-Quarters Cover (+5 bonus to AC and Dexterity saving throws), and Total Cover (can’t be targeted directly). If behind more than one degree of cover, a target benefits only from the most protective degree. See also chapter 1 (“Combat”).
Dagger of Blindsight: This rare magic item requires attunement. A creature attuned to it gains blindsight out to a range of 30 feet. The dagger has a saw-toothed edge and a black pearl nested in its pommel.
Blindsight: If you have Blindsight, you can see within a specific range without relying on physical sight. Within that range, you can see anything that isn’t behind Total Cover even if you have the Blinded condition or are in Darkness. Moreover, in that range, you can see something that has the Invisible condition.
Minor Illusion: Cantrip, Casting Time 1 Action, Range/Area 30 ft. (5 ft. *) Components S, M, Duration 1 Minute, School Illusion, Attack/Save None: You create a sound or an image of an object within range that lasts for the duration. See the descriptions below for the effects of each. The illusion ends if you cast this spell again. If a creature takes a Study action to examine the sound or image, the creature can determine that it is an illusion with a successful Intelligence (Investigation) check against your spell save DC. If a creature discerns the illusion for what it is, the illusion becomes faint to the creature. Sound. If you create a sound, its volume can range from a whisper to a scream. It can be your voice, someone else’s voice, a lion’s roar, a beating of drums, or any other sound you choose. The sound continues unabated throughout the duration, or you can make discrete sounds at different times before the spell ends. Image. If you create an image of an object—such as a chair, muddy footprints, or a small chest—it must be no larger than a 5-foot Cube. The image can’t create sound, light, smell, or any other sensory effect. Physical interaction with the image reveals it to be an illusion, since things can pass through it.
Tasha's Hideous Laughter: Level 1st, Casting Time 1 Action, Range/Area 30 ft., Components V, S, M, Duration Concentration 1 Minute, School Enchantment, Attack/Save WIS Save: One creature of your choice that you can see within range makes a Wisdom saving throw. On a failed save, it has the Prone and Incapacitated conditions for the duration. During that time, it laughs uncontrollably if it’s capable of laughter, and it can’t end the Prone condition on itself. At the end of each of its turns and each time it takes damage, it makes another Wisdom saving throw. The target has Advantage on the save if the save is triggered by damage. On a successful save, the spell ends. Using a Higher-Level Spell Slot. You can target one additional creature for each spell slot level above 1.
Fog Cloud: Level 1st, Casting Time 1 Action, Range/Area 120 ft. (20 ft. ), Components V, S, Duration Concentration 1 Hour, School Conjuration, Attack/Save None: You create a 20-foot-radius Sphere of fog centered on a point within range. The Sphere is Heavily Obscured. It lasts for the duration or until a strong wind (such as one created by Gust of Wind) disperses it. Using a Higher-Level Spell Slot. The fog’s radius increases by 20 feet for each spell slot level above 1.
Cover: The accompanying diagrams illustrate cover on squares or hexes. To determine whether a target has cover against an attack or other effect, choose a corner of the attacker’s space or the point of origin of an area of effect. Then trace imaginary lines from that corner to every corner of any one square the target occupies. If one or two of those lines are blocked by an obstacle (including a creature), the target has Half Cover. If three or four of those lines are blocked but the attack or effect can still reach the target (such as when the target is behind an arrow slit), the target has Three-Quarters Cover.

Naturally Stealthy (Halfling trait): You can take the Hide action even when you are obscured only by a creature that is at least one size larger than you.
Cunning Action (Rogue Class Feature at level 2): Your quick thinking and agility allow you to move and act quickly. On your turn, you can take one of the following actions as a Bonus Action: Dash, Disengage, or Hide.
Magical Ambush (Rogue Subclass Feature at level 9): If you have the Invisible condition when you cast a spell on a creature, it has Disadvantage on any saving throw it makes against the spell on the same turn.
Hide [Action]: With the Hide action, you try to conceal yourself. To do so, you must succeed on a DC 15 Dexterity (Stealth) check while you’re Heavily Obscured or behind Three-Quarters Cover or Total Cover, and you must be out of any enemy’s line of sight; if you can see a creature, you can discern whether it can see you. On a successful check, you have the Invisible condition. Make note of your check’s total, which is the DC for a creature to find you with a Wisdom (Perception) check. The condition ends on you immediately after any of the following occurs: you make a sound louder than a whisper, an enemy finds you, you make an attack roll, or you cast a spell with a Verbal component.
Invisible [Condition]: While you have the Invisible condition, you experience the following effects. Surprise. If you’re Invisible when you roll Initiative, you have Advantage on the roll. Concealed. You aren’t affected by any effect that requires its target to be seen unless the effect’s creator can somehow see you. Any equipment you are wearing or carrying is also concealed. Attacks Affected. Attack rolls against you have Disadvantage, and your attack rolls have Advantage. If a creature can somehow see you, you don’t gain this benefit against that creature.
Heavily Obscured: You have the Blinded condition while trying to see something in a Heavily Obscured space. See also “Blinded,” “Darkness,” and chapter 1 (“Exploration”).
Blinded [Condition]: While you have the Blinded condition, you experience the following effects. You can’t see and automatically fail any ability check that requires sight. Attack rolls against you have Advantage, and your attack rolls have Disadvantage.
Cover: Cover provides a degree of protection to a target behind it. There are three degrees of cover, each of which provides a different benefit to a target: Half Cover (+2 bonus to AC and Dexterity saving throws), Three-Quarters Cover (+5 bonus to AC and Dexterity saving throws), and Total Cover (can’t be targeted directly). If behind more than one degree of cover, a target benefits only from the most protective degree. See also chapter 1 (“Combat”).
Dagger of Blindsight: This rare magic item requires attunement. A creature attuned to it gains blindsight out to a range of 30 feet. The dagger has a saw-toothed edge and a black pearl nested in its pommel.
Blindsight: If you have Blindsight, you can see within a specific range without relying on physical sight. Within that range, you can see anything that isn’t behind Total Cover even if you have the Blinded condition or are in Darkness. Moreover, in that range, you can see something that has the Invisible condition.
Minor Illusion: Cantrip, Casting Time 1 Action, Range/Area 30 ft. (5 ft. *) Components S, M, Duration 1 Minute, School Illusion, Attack/Save None: You create a sound or an image of an object within range that lasts for the duration. See the descriptions below for the effects of each. The illusion ends if you cast this spell again. If a creature takes a Study action to examine the sound or image, the creature can determine that it is an illusion with a successful Intelligence (Investigation) check against your spell save DC. If a creature discerns the illusion for what it is, the illusion becomes faint to the creature. Sound. If you create a sound, its volume can range from a whisper to a scream. It can be your voice, someone else’s voice, a lion’s roar, a beating of drums, or any other sound you choose. The sound continues unabated throughout the duration, or you can make discrete sounds at different times before the spell ends. Image. If you create an image of an object—such as a chair, muddy footprints, or a small chest—it must be no larger than a 5-foot Cube. The image can’t create sound, light, smell, or any other sensory effect. Physical interaction with the image reveals it to be an illusion, since things can pass through it.
Tasha's Hideous Laughter: Level 1st, Casting Time 1 Action, Range/Area 30 ft., Components V, S, M, Duration Concentration 1 Minute, School Enchantment, Attack/Save WIS Save: One creature of your choice that you can see within range makes a Wisdom saving throw. On a failed save, it has the Prone and Incapacitated conditions for the duration. During that time, it laughs uncontrollably if it’s capable of laughter, and it can’t end the Prone condition on itself. At the end of each of its turns and each time it takes damage, it makes another Wisdom saving throw. The target has Advantage on the save if the save is triggered by damage. On a successful save, the spell ends. Using a Higher-Level Spell Slot. You can target one additional creature for each spell slot level above 1.
Fog Cloud: Level 1st, Casting Time 1 Action, Range/Area 120 ft. (20 ft. ), Components V, S, Duration Concentration 1 Hour, School Conjuration, Attack/Save None: You create a 20-foot-radius Sphere of fog centered on a point within range. The Sphere is Heavily Obscured. It lasts for the duration or until a strong wind (such as one created by Gust of Wind) disperses it. Using a Higher-Level Spell Slot. The fog’s radius increases by 20 feet for each spell slot level above 1.
Strategy: On the Rogue's turn they will move to a Spot, cunning action hide as a bonus action, and attempt to cast an upcast 3rd level Tasha's Hideous Laughter spell on as many foes they can see up to a maximum of three foes, with the intent to use Magical Ambush to impose Disadvantage on the initial saving throw against Tasha's Hideous Laughter (but not on any following saving throws that creature makes as it will not be made on the same turn).
The Spot they move to will change the scenario each time. It might be an existing Fog Cloud spell (which they can see through because of their Dagger of Blindsight), an existing Minor Illusion spell with two walls (cast on a prior round), behind an ally at least one size larger than them (trying to use naturally stealthy), or it might be behind a cart large enough to provide some meaningful cover against foes (halfling is 5 feet tall, cart is at least 4'2" feet tall), or the corner of a building.
How would you resolve this strategy for each foe in each of these depicted scenarios which each lists a different Spot:
Scenario 1: The Cart, halfling PC is #4, foes are 1, 2 and 3, 5 is just an ally

Scenario 2: The Ally, halfling PC is #4, Ally is #5, foes are 1 and 2

Scenario 3: The Fog Cloud

Scenario 4: The Illusion, minor illusion is the red wall next to PC

Scenario 5: The Corner.

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