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Imagine an Oath of Vengeance Paladin 3 / Hexblade 1. This is the big boss, and the character wants to use both Vow of Enmity and Hexblade's Curse on the same target.

Vow of Enmity gives advantage on all attack rolls against the target. Hexblade's Curse gives +2 (proficiency bonus) damage on all attacks, and crits on 19-20. Assume the character will close to melee distance in the first round of combat. Since both features require a bonus action to activate, the character must activate one during the first round of combat, and one during the second round.

Which one should the character activate first?

Does the answer change if the character has Extra Attack?

Does the answer change if the extra damage (i.e. proficiency bonus) from Hexblade's Curse is higher?

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    \$\begingroup\$ I assume you are asking which will cause most damage? \$\endgroup\$
    – SeriousBri
    Commented Dec 16, 2021 at 8:24
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    \$\begingroup\$ We need more information. The more the better. You character’s ability scores and weapon of choice are probably necessary. Even better would be the boss’s armor class and hit points. \$\endgroup\$ Commented Dec 16, 2021 at 9:00
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    \$\begingroup\$ Well - obviously I thought this question was possibly to usefully answer in the general case, so I think it could be reopened. A very specific answer could of course be produced if the OP gives us an exact build, though I think my analysis shows that at the low level given in the question it is unlikely to make a practical difference to the answer. \$\endgroup\$
    – Carcer
    Commented Dec 16, 2021 at 12:25
  • \$\begingroup\$ @Carcer We can't really answer a question where we don't understand the goal — we don't even know if they want to optimise for damage. We could instead also answer from a resource management standpoint entirely valid. \$\endgroup\$
    – Akixkisu
    Commented Dec 17, 2021 at 3:52

1 Answer 1

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Vow of Enmity at low levels, eventually shifting to Hexblade's Curse at the highest levels

Firstly, a few observations about how these two abilities compare to each other in various circumstances.

  • The easier it is to hit the enemy, the less benefit we get from advantage - so Vow of Enmity becomes less useful as our attack bonus increases or enemy AC decreases
  • The more damage our attack does normally, the less relative benefit we get from a couple points of extra damage - so Hexblade's Curse becomes less useful if we use a bigger weapon or have a higher damage modifier
  • Our chance to crit is slightly better with Hexblade's Curse - a 10% chance with expanded crit range vs. a 9.75% chance with advantage - so it has a very slight edge in terms of producing crits we can use to nova a divine smite on, but only slightly so
  • Advantage will tend to make our damage more reliable since it usually greatly reduces the chance of whiffing entirely
  • How many attacks we have (due to extra attack or any similar feature) is irrelevant to this damage analysis since each individual attack is affected the same way
  • The healing benefit of Hexblade's Curse almost certainly won't be relevant in the first round of combat and we'll have it active by the second round either way, so for that purpose it doesn't really matter which order we activate them in

Now, some numbers! I used this anydice script to calculate expected damage - hopefully it is obvious how you would modify it to change the parameters of the attack.

Basic Hexadin

Let's say our vengeful hexadin is using a longsword one-handed, has +2 proficiency and a +3 charisma modifier. That means a base damage of 1d8+3 and a +5 attack modifier. Running the numbers in my script against enemies of various ACs, the following values for expected damage fall out:

Enemy AC Normal Damage Vow of Enmity Hexblade's Curse
5 7.35 7.92 9.475
10 6.225 7.639 8.05
15 4.35 6.42 5.675
20 2.475 4.264 3.3
25 0.6 1.17 1.4

As we can see, when the enemy is extremely easy to hit the benefit of advantage is smaller and the damage bonus from Hexblade's curse is greater. However, as the enemy AC increases, the greater reliability of hitting with advantage overtakes the benefit of the bonus damage. In this case the exact crossover point is AC 12; then it becomes better to use Vow of Enmity. It also seems extremely unlikely that a boss-type enemy will have an AC worse than 12, so absent any other information, we'd have to assume that Vow of Enmity is the appropriate first move.

However, there is an inversion when going up against an extremely high AC; once it becomes so difficult to hit that we only hit on a crit (AC 25 in this case), Hexblade's Curse becomes the better option again, since the hit chance improvement is nearly identical and the hit just does more damage.

Critical Hitadin

What about if we add a special proviso that if we critically hit, we'll throw in a 1st level divine smite for a delicious 4d8 extra damage? (In my script, you can do this by adding 4d8 to the CRITDAM parameter.) Expected damage goes up a bit:

Enemy AC Normal Damage Vow of Enmity Hexblade's Curse
5 8.245 9.675 11.275
10 7.125 9.394 9.85
15 5.25 8.175 7.475
20 3.375 6.019 5.1
25 1.5 2.925 3.2

But the relative value of each approach stays similar, and in fact even in this scenario the crossover point is the same. The 0.25% difference in crit chance between the two features is just so small that it makes nearly no difference to the calculation of which is better.

Optimal Hexadin

Now consider a different set of parameters; our more-optimised vengeful hexadin is using their longsword two-handed and has a +5 charisma modifier, so they're doing 1d10+5 base damage and have a +7 to hit. Does this change the outcome?

Enemy AC Normal Damage Vow of Enmity Hexblade's Curse
5 10.25 11.01 12.425
10 9.725 10.931 11.8
15 7.1 9.75 8.675
20 4.475 7.256 5.55
25 1.85 3.45 2.42
30 0.8 1.56 1.8

As it turns out, no. Obviously our damage is higher overall, but the same relationship holds that once the enemy has a reasonable AC, advantage is better. In fact, the crossover point in this case is still AC 12, and it remains true that Hexblade's Curse only takes over again once we need a crit to hit at AC 27.

Mid-tier Hexadin

Let's add a few levels and some magical equipment to our character. How about a +4 proficiency modifier, a +5 charisma bonus and a +1 magic longsword? Now we're doing 1d10+6 base damage and have a +10 to hit.

Enemy AC Normal Damage Vow of Enmity Hexblade's Curse
5 11.2 12.008 15.275
10 11.2 12.008 15.275
15 9.475 11.576 12.95
20 6.6 9.708 9.075
25 3.725 6.401 5.2
30 0.85 1.658 2.1

Because of our high attack bonus, for ACs of 10 or lower we only miss on a crit so those rows in the table will be the same, but above that we see a similar relationship play out. This time the break point has moved to AC 18 - below that, Hexblade's Curse is better, but above that, the Vow of Enmity wins out, with the caveat again that once we only hit on a crit the Curse regains the upper hand.

AC 18 is in the range of what you would expect for a boss monster at that tier, so at this point without actually knowing what the enemy's AC is, we're hard-pressed to guess which ability to activate first. If it looks particularly well-armoured then go for the Vow of Enmity, if not then pop the Hexblade's Curse. It will be useful to have allies who attack before we do so we have a chance at figuring out the enemy's AC before we have to act.

Epic Hexadin

Let's go wild. Now our vengeful hexadin is level 20, has a +3 magic longsword they're wielding two-handed, a +6 proficiency modifier and has somehow arranged for themselves a +6 charisma modifier, so they've got 1d10+9 base damage and a +15 attack bonus. Let's say they've even taken the 11 paladin levels required to get Improved Divine Smite, for an extra 1d8 base damage on all attacks. How are the numbers now?

Enemy AC Normal Damage Vow of Enmity Hexblade's Curse
5 18.55 19.928 24.75
10 18.55 19.928 24.75
15 18.55 19.928 24.75
20 15.7 19.215 21
25 10.95 16.128 14.75
30 6.2 10.665 8.5
35 1.45 2.828 3.5

This time the crossover point is AC 23, which is extremely high for 5e; a search of D&D Beyond indicates there are only 8 published stat blocks with an AC of 23 or higher. If we're fighting Tiamat or the Tarrasque, the Vow of Enmity is more useful; but for a foe in the more likely 19-21 AC range, the Hexblade's Curse is better.

If we tune down our parameters a bit, by dropping to a +1 weapon and a +5 charisma bonus, the breakpoint only goes down to 21, which is still higher than the majority of monsters (the DMG's guidance indicates that an AC of 19 is typical for monsters at CR 17+). If we instead alter our level distribution to favour the Warlock side and lose the bonus 1d8 base damage from Improved Divine Smite, the breakpoint increases to AC 25! (recall that Hexblade's Curse provides a relatively larger benefit when our attack has less base damage.)

Conclusion / TL;DR

The relative value of these two features will change as you level, partly because the Hexblade's Curse bonus damage improves as you level while the Vow of Enmity does not change, and partly because your attack bonus will probably scale up faster than enemy AC does. For any given build there is an enemy AC breakpoint above which the Vow of Enmity is best and below which the Hexblade's Curse is better.

At low levels, in any realistic combat encounter you will see the biggest improvement in expected damage from using Vow of Enmity; since the bonus damage from Hexblade's Curse is so small, the improved reliability of damage from advantage trumps it. The AC breakpoint will be so low that you would expect any significant foe you face to have an AC higher than that.

At the mid-tier, it becomes harder to judge which is most useful, since the break-even point between the two will be inside the range of ACs you expect your foes to have.

At very high levels, the increased damage from Hexblade's Curse has become significant enough that it is likely the superior option in most encounters; the AC breakpoint is high enough that it is probably above the AC of your enemy.

For any given build, though, you can use a script like mine to work out what the actual enemy AC breakpoint is. The assumptions I've made in my calculations above seem reasonable for establishing a rule of thumb, but once you're out of the low levels, which option is actually best for you will depend on the specifics of your character and the enemy you face.

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    \$\begingroup\$ I love how you addressed the tier / advancement examples to answer the question beyond the 3/1 MC ... bravo. 😊👍 \$\endgroup\$ Commented Dec 16, 2021 at 19:21
  • \$\begingroup\$ Very useful analysis, and thanks for the link to the anydice script. \$\endgroup\$ Commented Dec 17, 2021 at 15:19
  • \$\begingroup\$ @RedGeomancer no worries. If you're so inclined, editing your question to clarify that you're interested in damage optimisation (as I have essentially assumed in my answer) should satisfy those stackizens who felt the question need more clarity and lead to a reopening. \$\endgroup\$
    – Carcer
    Commented Dec 18, 2021 at 23:02
  • \$\begingroup\$ @Carcer After a couple of unsuccessful recent attempts to fix questions to get them reopened I would rather bash my head against a wall. Even though the question is closed, I was able to select this as the correct answer. I doubt we will get a better one, so there is not much value in reopening. \$\endgroup\$ Commented Dec 25, 2021 at 0:00

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