Imagine a villain has taken a character prisoner and is forcing them to stay awake several days (using the optional rules on Xanathar's Guide p. 78 about spending 24 hours without a long rest) in the hopes of getting them to level 3 exhaustion so he can force them to make a saving throw at disadvantage.

(The specific situation that came up is a villain with a prison full of people affected by the feeblemind spell, who keeps meticulous records and tries to make sure they're at level 3 exhaustion for the 30-day save to shake it off.)

Is there a way for him to tell for sure whether or not they made their Con save to avoid exhaustion?

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    \$\begingroup\$ @krb That could be a potential answer to this, but not every table treats metagaming the same way. Let's not judge them on their playstyle and just answer the question. \$\endgroup\$
    – NautArch
    Aug 1 '19 at 12:13
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    \$\begingroup\$ @Tektotherriggen That looks like the beginning of an answer to the question. \$\endgroup\$ Aug 1 '19 at 13:15

Not with full accuracy, but a Skill Check is appropriate

The Exhaustion levels and the Disadvantage on the Saving throw are an abstraction meant to model real-life effects, in this case a weakened mental state from sleep deprivation. Therefore, what a villain knows is only "At a certain level of sleep deprivation, people can't resist my spell as effectively" instead of the very precise "After exactly X hours without sleep, assuming they didn't succeed in their CON save, they have to make their saving throw at an Disadvantage".

Sleep deprivation has a few external symptoms and associated behaviour changes. It would therefore be appropriate to make Wisdom(Medicine) checks to use these symptoms to gauge their exhaustion level. While the Villain doesn't know what Level 3 Exhaustion is (it's an abstraction for the players), he will sure be able to tell between somebody who is still more alert (because they made their CON saves) and somebody who's non-stop hallucinating from lack of sleep. Failing that Wisdom(Medicine) check means that the Villain mis-judges the state their victim is in, either thinking they're already too far along (allowing them make a normal save instead) or thinking they're not that far gone yet (which puts them at danger of dying or at least longer-lasting health effects).

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    – V2Blast
    Aug 1 '19 at 9:03
  • \$\begingroup\$ I had initially really liked this, but I think the mechanics of doing this are unclear and this feels more like an idea generation rather than a tested solution (and we try to support our ideas with tableplay you've done or seen.) The problem I see is that a 'failed' check isn't clear on they think they're more or less exhausted than they are. Less exhausted than they are could lead to character death, while more could lead to the player not getting disadvantage on their character's save. \$\endgroup\$
    – NautArch
    Aug 1 '19 at 12:54
  • \$\begingroup\$ This is an answer showing how a DM can apply the "Using Ability Scores" instructions in Chapter 7 of the PHB. It is a nice synthesis of what's in the PHB and what's in the DMG on how to handle ability checks. (I'd recommend a reference to the DMG treatment of how to handle ability checks, since there is some guidance there) \$\endgroup\$ Aug 1 '19 at 13:12

This is possible, but likely requires at least a Bard and a Fighter

Note: this is an incredibly meta-gaming heavy answer and would likely not be an enjoyable experience if done to a player character due to that. I took this approach because the entire idea of a villain understanding "exhaustion levels" is meta-gaming.

What is needed:

An understanding of the exhaustion levels:

1: Disadvantage on ability checks
2: Speed halved
3: Disadvantage on attacks rolls and saving throws
4: Hit point maximum halved
5: Speed reduced to 0
6: Death

A way to prevent the prisoner from dying

One way you could do this is through the death ward spell whose description states:

You touch a creature and grant it a measure of protection from death.
The first time the target would drop to 0 hit points as a result of taking damage, the target instead drops to 1 hit point, and the spell ends...

This allows you to damage the prisoner (required later) and guarantee that it will not kill them, this also allows you to reduce the prisoner to 1 hit point.

Knowing which exhaustion level a prisoner is at

If a prisoner were at exhaustion level 6:
This would likely be obvious, but if not you could use the speak with dead spell to determine this as it only targets corpses.

If a prisoner were at exhaustion level 5:
You could use the dissonant whispers spell, whose description states:

On a failed save, it takes 3d6 psychic damage and must immediately use its reaction , if available, to move as far as its speed allows away from you...

You could use this spell until it damaged your prisoner (likely a visible effect), and if they did not move then you would know they are at exhaustion level 5.
It is possible that they would have already used their reaction on something else and this is why the slow spell is needed as its description states:

An affected target's speed is halved, it takes a −2 penalty to AC and Dexterity saving throws, and it can't use reactions...

You could prevent the creature from using reactions through this spell, and could drop concentration on it just before dissonant whispers is cast, thus guaranteeing that if they fail the save they will try to move.
Additionally, perhaps the prisoner taking damage is not particularly visible, if they took damage you could use the identify spell whose description states:

If you instead touch a creature throughout the casting, you learn what spells, if any, are currently affecting it...

This allows you to know whether a creature is suffering from slow or benefiting from death ward (after taking damage they would no longer be under the affects of death ward).

If a prisoner were at exhaustion level 4: This becomes more difficult to figure out...
A Battle Master Fighter has the Know Your Enemy feature which states:

If you spend at least 1 minute observing or interacting with another creature outside combat, you can learn certain information about its capabilities compared to your own. The DM tells you if the creature is your equal, superior, or inferior in regard to two of the following characteristics of your choice:
Current hit points...

You could restore a creature to its hit point maximum using healing spells such as cure wounds but if that is not an option because the prisoner is an undead or construct you could instead use potions of healing which have no such restriction.
Through healing and the death ward spell you can also manipulate your Fighter's current hit points. This allows you to determine roughly the prisoner's maximum, and thus you could also determine if their hit point maximum had been halved.

If a prisoner were at exhaustion level 1 or 0:
You could roughly determine their speed using the dissonant whispers spell. This allows you to know whether they are at exhaustion level 2 because they would only move half of the distance they did at levels 1 and 0.

If a prisoner were at exhaustion level 3:
Its speed would be halved but its hit point maximum would not, as explained above, you could determine both of these things.

You can force a creature to go to exhaustion level 0 by using the greater restoration repeatedly; its description states:

You imbue a creature you touch with positive energy to undo a debilitating effect. You can reduce the target's exhaustion level by one...

I could not think of any real way to determine if a creature is at specifically exhaustion level 1, but you could force them to go to it by using greater restoration when they are at level 2.

Thus you can determine which level of exhaustion any given prisoner is at (though significant setup and bookkeeping is required) except level 1 which you could force them to be at if you so desired.

A notable exception: Deafened creatures are not affected by dissonant whispers so some of this strategy would not work against them. The spell's description states:

A deafened creature automatically succeeds on the save...

One possible way to avoid this problem is by using the fear spell instead of dissonant whispers. It's description states:

While Frightened by this spell, a creature must take the Dash action and move away from you by the safest available route on each of its turns

This would work as an alternative but if a prisoner were immune to frighten it would not. There is also the case that a creature could pretend to fail a save against the spell and run away from you regardless in which case you would need somebody else to use the identify spell.

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    \$\begingroup\$ May or may not be worth addressing if this would be 'fun' for the player. \$\endgroup\$
    – NautArch
    Aug 1 '19 at 13:08
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    \$\begingroup\$ The villain has taken the player character prisoner. So the villain(s) would be doing this to a player character. \$\endgroup\$
    – NautArch
    Aug 1 '19 at 13:09
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    \$\begingroup\$ @markwells I don't understand your question. The asker wanted a way to track exhaustion, I provided one? \$\endgroup\$ Aug 1 '19 at 17:23
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    \$\begingroup\$ The villain hasn't taken a player character prisoner, this is an off-screen thing happening to NPCs. \$\endgroup\$ Aug 1 '19 at 21:10
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    \$\begingroup\$ @EttinaKitten: That's a very important distinction (that it's being done by the NPC villain to other NPCs). You should edit that into your original question. \$\endgroup\$
    – V2Blast
    Aug 2 '19 at 5:25

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