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What would be the challenge rating for this custom NPC enemy? It's definitely more than 8 but I don't know what. In essence, it's a Drow Elite Warrior combined with an Assassin:

Drow Elite Assassin

Medium humanoid (elf), neutral evil

Armor Class 16 (Studded Leather)
Hit Points 75 (10d10 + 20)
Speed 30 ft.

\begin{array}{cccccc} \text{STR} & \text{DEX} & \text{CON} & \text{INT} & \text{WIS} & \text{CHA} \\ 14\;(+2) & 18\;(+4) & 14\;(+2) & 12\;(+1) & 14\;(+2) & 12\;(+1) \end{array}

Saving Throws Dex +7, Con +5, Int +4, Wis +5
Skills Perception +4, Stealth +10
Damage Resistance poison
Senses darkvision 120 ft., passive Perception 14
Languages Common, Elvish, Undercommon
Challenge 8 (3900 XP)

Fey Ancestry. The Assassin has advantage on saving throws against being charmed, and magic can't put the Assassin to sleep.

Sunlight Sensitivity. While in sunlight, the Assassin has disadvantage on attack rolls, as well as on Wisdom (Perception) checks that rely on sight.

Assassinate. During its first turn, the Assassin has advantage on attack rolls against any creature that hasn't taken a turn. Any hit the Assassin scores against a surprised creature is a critical hit.

Evasion. If the Assassin is subjected to an effect that allows it to make a Dexterity saving throw to take only half damage, the Assassin instead takes no damage if it succeeds on the saving throw, and only half damage if it fails.

Sneak Attack (1/Turn). The Assassin deals an extra 13 (4d6) damage when it hits a target with a weapon attack and has advantage on the attack roll, or when the target is within 5 feet of an ally of the Assassin that isn't incapacitated and the Assassin doesn't have disadvantage on the attack roll.

Innate Spellcasting. The Assassin's spellcasting ability is Charisma (spell save DC 12). It can innately cast the following spells, requiring no material components:

  • At will: dancing lights
  • 1/day each: darkness, faerie fire, levitate (self only)

Actions

Multiattack. The Assassin makes 2 attacks.

Drow-poisoned Dagger. Melee or Ranged Weapon Attack: +7 to hit, reach 5 ft., or range 20/60 ft., one target. Hit: 6 (1d4+4) piercing damage. A creature subjected to this poison must succeed on a DC 13 Constitution saving throw or be poisoned for 1 hour. If the saving throw fails by 5 or more, the creature is also unconscious while poisoned in this way. The creature wakes up if it takes damage or if another creature takes an action to shake it awake.

Reactions

Parry. The Assassin adds 3 to its AC against one melee attack that would hit it. To do so, the Assassin must see the attacker and be wielding a melee weapon.

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    \$\begingroup\$ Can you comment on which part(s) of the canonical method for calculating CR (DMG pp.274-279) is(are) giving you trouble? \$\endgroup\$ – nitsua60 Nov 11 '16 at 3:33
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    \$\begingroup\$ Including what methods you've tried, are having trouble with, and what research you've done in order to try and answer this question yourself (as per nitsua60's comment whether you've looked through/tried the methods in the DMG) would go a long way in helping the community tailor answers to better help you and avoid repeating things you've already done. \$\endgroup\$ – Purple Monkey Nov 11 '16 at 3:41
  • \$\begingroup\$ How do you know it's "definitely stronger than 8"? My current AL party of L6/7 would drop this thing in a round; the martial-types among us are often doing 30-40 damage per turn. \$\endgroup\$ – nitsua60 Nov 11 '16 at 3:58
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I get CR=4, using the DMG and some generous (to the NPC) assumptions.

Defensive CR based off of HP is 1, bump that up by 1 for the (relatively) high AC.

Offensive CR based off three-round damage is 4, bump that up by 1 of the (relatively) high attack bonus. This assumes that its first-round attacks are with surprise (auto-crit both attacks, advantage creates SA on the first), that it gets SA on each of the two subsequent rounds, and that all six attacks hit.

Innate spellcasting and poison resistance didn't factor in.

So that's a final CR of 3.5, rounded up to 4.

I didn't factor in the possibility of its poison attack knocking a party member unconscious. I figure it's a 25% chance of happening (DC13 CON save is practically a coin toss since everyone puts at least something into CON, so failing by 5 is ~1/4 probability), which means it's likely to happen once during those three rounds of simulated combat. Dropping one party member unconscious during a battle doesn't strike me as that far off the usual battle-path as to need separate treatment.


Now I also get a lower-than-8 CR when running that procedure against the MM Assassin statblock, off of which you've based this character. That implies that playtesting showed the Assassin's features that I've ignored above do impact the level of character that the Assassin threatens. So while I've already rounded up and granted your Drow Assassin some generous assumptions it may make sense to further bump the CR by 1, calling it a CR 5.

But playtesting is the only way to be really sure. Recruit a friend, make up your "representative" group of 4 PCs at different levels, and run some mock combats.

(Are there more pre-generated characters for the D&D Starter Set available? may help; particularly the group of characters statted levels 1 through 10 available from WotC.)

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It's weaker than CR 8

You took away the extra 7d6 poison damage from the Assassin stat block (MM p.343), which gives it a lot of its damage per round and weakens this particular creature.

If I were you, I'd take the Assassin stat block and just add the Drow features in DMG 282. The creature's Dexterity Score increases by 2 but it doesn't have an effect on the Challenge Rating. All the attacks from the Assassin should stay the same.

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