OK, here’s a quickie post in response to a reader who pointed out that I haven’t yet taken a look at two non-player characters from the Monster Manual: the scout and the spy.
Scouts are spotters and lookouts. With proficiency in Perception and Stealth, they could be effective ambush attackers, but that’s not their job. Their job is to gather information and return with it; combat is an undesirable complication. Consequently, if they attack at all, they prefer strongly to do so at range.
Eighty percent of the humanoids they encounter will have a speed of 30 feet. Of the remainder, most will have a speed of either 25 or 35 feet. Therefore, they don’t position themselves any closer than 75 feet to their targets unless they absolutely have to, and if they have a good view, they’re content to stay as far as 150 feet away. They can attack at these distances without disadvantage, but they’re not assassins. They attack only in self-defense.
Whether they do even this much depends on the speed of any foe who sees and pursues them. If the subjects of their reconnaissance have a speed of 30 feet or slower, they take potshots (Multiattack, Longbow × 2) at pursuers who are still more than 75 feet away at the start of the scouts’ turn. If the pursuers are closer or faster, scouts Dash away. If more than one opponent manages to get within melee reach, or if they can’t afford to take even a single hit, they Disengage—they have the training to do so.
Scouts only drop their bows and draw their swords when they’re surrounded, with no avenue of escape. If they have no reason to think they’ll be killed if they’re captured, they may choose to surrender rather than fight.
Spies are like scouts, but more hands-on. Rather than simply observe from a distance, they often have to operate in their enemies’ midst. Spies aren’t assassins either, but from time to time, if they’re caught, they may have to fight someone to the death. To make this feasible, it’s extremely important that they find or manufacture some source of advantage on each attack roll, so that they can maximize their damage via Sneak Attack, because they’re not likely to have allies on the scene to distract their targets. If they can’t do that, they need to head for the door.
Sadly, there’s nothing in the spy stat block that enables a spy to blind, paralyze, knock prone, restrain or stun an opponent. Nor does it include any sense that would allow the spy to see its opponent in darkness. This is super easy to handwave: All you have to do is decide that your spy belongs to a race with darkvision. But this “solution” leads to a game world arms race in which only races with darkvision are spies, so I’m disinclined to go there.
One alternative is to get out of sight, then use Cunning Action to Hide as a bonus action, then Ready a Shortsword attack, counting on the enemy to pursue. But this isn’t ideal, either. It costs spies the second melee attack they’d otherwise get by using Multiattack on their own turn, so that, at best, they deal 3d6 + 2 damage (on average, 12) rather than 2d6 + 4 (on average, 11). What they really want is a second Shortsword attack and Sneak Attack damage, and that can happen only on their own turn.
Ah, here’s a loophole: The spy’s Multiattack specifies “two melee attacks,” not “two Shortsword attacks.” That means spies can grapple and shove as part of their attack combos!
If a spy can knock its opponent prone, they then get advantage on the follow-up grapple attack [Nope. A grapple is a contested ability check, not an attack roll.] , which if successful Knocking an opponent prone, then grappling them reduces the opponent’s speed to 0, making them unable to get up. On its next turn, the spy can then stab with impunity. Alas, there’s a major downside. The spy’s Strength is only 10. That doesn’t bode well for the initial shoving attack. If they can get advantage on that attack, maybe they can make it work—but if they have advantage, why don’t they just stab and deal Sneak Attack damage instead? Grapple/shove, if it can be made to work at all, is preferable only if the spy doesn’t want to kill the target—if they want instead to extract information under the threat of stabbing. (Which would be more effective if the spy had proficiency in Intimidation.)
Unless a spy gets exceptionally lucky, there’s no way out of this mess. Not even Cunning Action offers spies a way to break line of sight, Hide, then attack at melee range in a single turn without being spotted again as they move in to strike. It looks like the only good application of the melee Multiattack/Sneak Attack combination is taking out guards in dim light, inasmuch as an already hidden spy can plausibly close the distance to its target without being spotted along the way. This maneuver deals 18 damage on average, 50 percent more than trying to do the same job from a distance with a hand crossbow.
No, if a spy is busted—and especially if a spy is busted by an entire party of player characters—its best recourse is to book it. Dodge isn’t a good retreat action for spies: their Armor Class is too low. They’re better off Disengaging when engaged in melee with more than one opponent or when they can’t afford to take a single hit, and Dashing when they can afford to take a single hit and/or their opponents are very likely to give chase. While retreating, they use Cunning Action to Hide as a bonus action as soon as they break line of sight, and they stay hidden as they complete their escape.
If they’re cornered, however, spies fight to the death. Captured spies are nearly always killed, or at least tossed in nasty dungeons to think about what they’ve done for a long time, and the reputations of the organizations they belong to hang on their members’ unwillingness to give up the secrets they’ve learned. This combination of factors produces a kind of zealotry that overrides their self-preservation impulses.