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Laurel
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Death isn't the only, or necessarily most useful, way to remove enemies from the fight

If keeping enemies alive for questioning, rehabilitating or even ransoming is useful in your games then the Sleep spell never loses it'sits usefulness - it just means you need to wear your enemies down more before you can use it.

My question here is -- at what level is the actual turning point reached, at which the spell, upcast to the highest level available, can be expected to lose usefulness to put to sleep (a) multiple opponents and (b) a single one?

The premise of your question seems to come more from a video games min maxing than a role play perspective. Sleep can down an enemy (or enemies) without killing them, letting them survive to be questioned later. Spells don't normally have the ability to deal non-lethal damage:

Sometimes an attacker wants to incapacitate a foe, rather than deal a killing blow. When an attacker reduces a creature to 0 hit points with a melee attack, the attacker can knock the creature out. The attacker can make this choice the instant the damage is dealt. The creature falls unconscious and is stable.

The usefulness of this utility depends on your game. I often play in/DM games where there is an element of uncovering mystery where questioning people is essential to uncovering information. In one game (level 7) we were investigating some robberies - after uncovering the next likely target we waited and ambushed the burglars. When the fight turned the captain fled faster than any of us could run (all those rogue dashes), we wanted to question them and the best ranged option we had to knock an opponent out at range was sleep. The story progressed smoother and, since the captain was the son of a noble family, we avoided some negative consequences the DM had planned for us if we had chosen to kill him.

Death isn't the only, or necessarily most useful, way to remove enemies from the fight

If keeping enemies alive for questioning, rehabilitating or even ransoming is useful in your games then the Sleep spell never loses it's usefulness - it just means you need to wear your enemies down more before you can use it.

My question here is -- at what level is the actual turning point reached, at which the spell, upcast to the highest level available, can be expected to lose usefulness to put to sleep (a) multiple opponents and (b) a single one?

The premise of your question seems to come more from a video games min maxing than a role play perspective. Sleep can down an enemy (or enemies) without killing them, letting them survive to be questioned later. Spells don't normally have the ability to deal non-lethal damage:

Sometimes an attacker wants to incapacitate a foe, rather than deal a killing blow. When an attacker reduces a creature to 0 hit points with a melee attack, the attacker can knock the creature out. The attacker can make this choice the instant the damage is dealt. The creature falls unconscious and is stable.

The usefulness of this utility depends on your game. I often play in/DM games where there is an element of uncovering mystery where questioning people is essential to uncovering information. In one game (level 7) we were investigating some robberies - after uncovering the next likely target we waited and ambushed the burglars. When the fight turned the captain fled faster than any of us could run (all those rogue dashes), we wanted to question them and the best ranged option we had to knock an opponent out at range was sleep. The story progressed smoother and, since the captain was the son of a noble family, we avoided some negative consequences the DM had planned for us if we had chosen to kill him.

Death isn't the only, or necessarily most useful, way to remove enemies from the fight

If keeping enemies alive for questioning, rehabilitating or even ransoming is useful in your games then the Sleep spell never loses its usefulness it just means you need to wear your enemies down more before you can use it.

My question here is -- at what level is the actual turning point reached, at which the spell, upcast to the highest level available, can be expected to lose usefulness to put to sleep (a) multiple opponents and (b) a single one?

The premise of your question seems to come more from a video games min maxing than a role play perspective. Sleep can down an enemy (or enemies) without killing them, letting them survive to be questioned later. Spells don't normally have the ability to deal non-lethal damage:

Sometimes an attacker wants to incapacitate a foe, rather than deal a killing blow. When an attacker reduces a creature to 0 hit points with a melee attack, the attacker can knock the creature out. The attacker can make this choice the instant the damage is dealt. The creature falls unconscious and is stable.

The usefulness of this utility depends on your game. I often play in/DM games where there is an element of uncovering mystery where questioning people is essential to uncovering information. In one game (level 7) we were investigating some robberies after uncovering the next likely target we waited and ambushed the burglars. When the fight turned the captain fled faster than any of us could run (all those rogue dashes), we wanted to question them and the best ranged option we had to knock an opponent out at range was sleep. The story progressed smoother and, since the captain was the son of a noble family, we avoided some negative consequences the DM had planned for us if we had chosen to kill him.

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Lio Elbammalf
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Death isn't the only, or necessarily most useful, way to remove enemies from the fight

If keeping enemies alive for questioning, rehabilitating or even ransoming is useful in your games then the Sleep spell never loses it's usefulness - it just means you need to wear your enemies down more before you can use it.

My question here is -- at what level is the actual turning point reached, at which the spell, upcast to the highest level available, can be expected to lose usefulness to put to sleep (a) multiple opponents and (b) a single one?

The premise of your question seems to come more from a video games min maxing than a role play perspective. Sleep can down an enemy (or enemies) without killing them, letting them survive to be questioned later. Spells don't normally have the ability to deal non-lethal damage:

Sometimes an attacker wants to incapacitate a foe, rather than deal a killing blow. When an attacker reduces a creature to 0 hit points with a melee attack, the attacker can knock the creature out. The attacker can make this choice the instant the damage is dealt. The creature falls unconscious and is stable.

The usefulness of this utility depends on your game. I often play in/DM games where there is an element of uncovering mystery where questioning people is essential to uncovering information. In one game (level 7) we were investigating some robberies - after uncovering the next likely target we waited and ambushed the burglars. When the fight turned the captain fled faster than any of us could run (all those rogue dashes), we wanted to question them and the best ranged option we had to knock an opponent out at range was sleep. The story progressed smoother and, since the captain was the son of a noble family, we avoided some negative consequences the DM had planned for us if we had chosen to kill him.