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How do multiple castings of Hex affect a creature?

This question has two parts related to the same spell and game mechanic.

Scenario 1:

The Three Warlocks walk into a tavern and spot their arch-enemy: the infamous paladin Sir Happy Wings. The paladin laughs out loud, drinks up the last of his ale, and slams his tankard onto the bar. The Three Warlocks and Sir Happy Wings exchange threatening glances.

They roll for initiative: all three warlocks end up with the same initiative; the paladin goes last.

The Three Warlocks have been bested by Sir Happy Wings in the past. They decide to work as a team and all three decide to cast Hex on the paladin on their individual turns, using a 1st-level spell slot. They want to minimise the Paladin's chances of making his Wisdom ability checks in the coming rounds.

What happens next...?

From what I understand, the Paladin will have all three Hex curses active at once. The rules about combining effects say that only one effect of Hex would affect the Paladin, even though multiple Hex spells could be active at the same time. (PHB p.205)

Sir Happy Wings feels down on his luck, but on his turn attacks one of the warlocks, rolls a natural 20 and thwacks the warlock. The warlock rolls the dice to find that, unfortunately for her, she has lost concentration, effectively ending her Hex spell.

Would the other two Hex spells still remain active?

Scenario 2:

Almost the same, only this time each of The Three Warlocks targets a different ability: Dexterity, Constitution and Wisdom.

In this case, how can we determine which of Sir Happy Wings ability checks is going to be affected by the Hex spell? The first one, or the last one? Or, we roll a die perhaps?

I know this is related to other questions, but I would like an explanation of how this game mechanic works with this particular spell. Thank you.

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RAW, only the last hex would give disadvantage

This requires some close reading of the PHB and some interpretation, but I'll quote the relevant section for reference here:

The effects of different spells add together while the durations of those spells overlap. The effects of the same spell cast multiple times don't combine, however. Instead, the most potent effect - such as the highest bonus - from those castings applies while their durations overlap. (PHB p. 205)

Note that this has actually been errata'd:

Combining Magical Effects (p. 205). In the first paragraph, the following sentence has been added to the first paragraph: “Or the most recent effect applies if the castings are equally potent and their durations overlap.”

And now, the hex spell:

You place a curse on a creature that you can see within range. Until the spell ends, you deal an extra 1d6 necrotic damage to the target whenever you hit it with an attack. Also, choose one ability when you cast the spell. The target has disadvantage on ability checks made with the chosen ability. (PHB p. 251)

If we look at the hex description, we see two distinct effects. One affects you, the caster, and causes you to deal more damage on attacks against a specific target. The second affects the target, and grants disadvantage on certain ability checks (I feel obligated to point out it doesn't affect saving throws). Note that the rules on combining magical effects applies to "effects of the same spell", not the entire spell itself. Thus, we can make the assumption that only the effects that are trying to combine will have to "fight" each other. As mentioned in this answer on hunter's mark, the first effect of dealing damage only affects the caster. The multiple castings do not stack and everything works out without conflict. However, the second effect affects the target, and therefore multiple castings will interfere with each other. As mentioned in this answer on similar spells, the most potent spell would take precedence even if the exact mechanics of the effects don't "stack" (i.e. even if the warlocks target different abilities).

What does this mean for your scenarios?

Scenario 1:

Each of the warlocks cast hex, targeting Wisdom checks (again, this won't affect the paladin's saving throws). The first effect, that of dealing extra damage, applies to each of the warlocks. The second effect however cannot stack, and only the most potent applies. Since they are all of the same potency, we rely on the errata to determine that whichever warlock happens to cast last has their spell go through. Dealing with simultaneous effects is completely DM dependent; some resolve speed ties through Dexterity bonuses, others go around the table clockwise, others allow the players to determine who goes first, etc. As V2Blast pointed out, Xanathar's Guide to Everything (p. 177) suggests the players decide. However the order is determined, only one of these warlocks is actually imposing disadvantage on Wisdom checks. This doesn't mean that the other warlocks' hexes are dispelled though - they simply have no effect.

So, the paladin breaks one of the warlock's concentration. Now, there are two hexes affecting the paladin. If the previously 'most recent' hex was the one that was broken, the next 'most recent' hex applies, since a dispelled hex is certainly less potent than an active one. It doesn't really matter whose hex is still up, since they all picked the same ability. The paladin still has disadvantage on Wisdom checks, and the unharmed warlocks still have damage bonuses on their attacks.

Scenario 2:

This one plays out exactly as above; the last hex takes precedence. Again, which one this is is up to the DM.

Hopefully this answers your question! I made sure to look around the internet before trying to give a RAW answer and there seems to be lots of confusion around similar spells. Perhaps in the next edition we'll have more clear definitions of words like effect and combine so we don't leave everything up to DM interpretation.

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    \$\begingroup\$ "Dealing with simultaneous effects is completely DM-dependent" - Xanathar's Guide to Everything (p. 77) does have an optional rule for resolving simultaneous effects: "If two or more things happen at the same time on a character or monster’s turn, the person at the game table — whether player or DM — who controls that creature decides the order in which those things happen. For example, if two effects occur at the end of a player character’s turn, the player decides which of the two effects happens first." \$\endgroup\$ – V2Blast Feb 4 at 10:01
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    \$\begingroup\$ It's perfectly fine to edit it into your answer to improve it! That's why I left the comment :) (If/when you do, I'll clean up the comments.) \$\endgroup\$ – V2Blast Feb 4 at 10:04
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    \$\begingroup\$ That's why I said "the unharmed warlocks still have damage bonuses on their attacks" \$\endgroup\$ – legodude5000 Feb 4 at 14:19
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    \$\begingroup\$ @legodude5000 Ah, I missed that. +1 either way. \$\endgroup\$ – TheLittlePeace Feb 4 at 14:26
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    \$\begingroup\$ Minor point but the order on which the spells are launched (and thus take effect) is perfectly determined, since by raw the initiative order is established prior to the first turn and "the players decide the order among their tied characters. ". \$\endgroup\$ – JFL Feb 4 at 19:22

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