New Edition, New Rogue - Comparing and contrasting the rogue's specialty.
I've thought hard about rogues in Dungeons and Dragons Third Edition, and its close cousin Pathfinder First Edition, for a long time (for example, see this 2014 screed on ways to deny your enemy her dexterity bonus to AC, or this 2005 screed on spells and sneak attacks.
But the pandemic gave me the chance to join a 5E campaign, and I played an arcane trickster from level 1 to level 12. Well, actually, I played a rogue/wizard with the AT specialty. But the point is, I became pretty familiar with 5E sneak attacks. They have interesting similarities and differences. So let's take a look at both.
First of all, consider the rules.
Third Edition (The Pathfinder rules are virtually identical): If a rogue can catch an opponent when he is unable to defend himself effectively from her attack, she can strike a vital spot for extra damage. The rogue’s attack deals extra damage any time her target would be denied a Dexterity bonus to AC (whether the target actually has a Dexterity bonus or not), or when the rogue flanks her target. This extra damage is 1d6 at 1st level, and it increases by 1d6 every two rogue levels thereafter. Should the rogue score a critical hit with a sneak attack, this extra damage is not multiplied. Ranged attacks can count as sneak attacks only if the target is within 30 feet. With a sap (blackjack) or an unarmed strike, a rogue can make a sneak attack that deals nonlethal damage instead of lethal damage. She cannot use a weapon that deals lethal damage to deal nonlethal damage in a sneak attack, not even with the usual -4 penalty. A rogue can sneak attack only living creatures with discernible anatomies—undead, constructs, oozes, plants, and incorporeal creatures lack vital areas to attack. Any creature that is immune to critical hits is not vulnerable to sneak attacks. The rogue must be able to see the target well enough to pick out a vital spot and must be able to reach such a spot. A rogue cannot sneak attack while striking a creature with concealment or striking the limbs of a creature whose vitals are beyond reach.
Fifth Edition: Beginning at 1st level, you know how to strike subtly and exploit a foe’s distraction. Once per turn, you can deal an extra 1d6 damage to one creature you hit with an attack if you have advantage on the attack roll. The attack must use a finesse or a ranged weapon. You don’t need advantage on the attack roll if another enemy of the target is within 5 feet of it, that enemy isn’t incapacitated, and you don’t have disadvantage on the attack roll. The amount of the extra damage increases as you gain levels in this class, as shown in the Sneak Attack column of the Rogue table. [1d6/2levels, same as 3E]
The similarities make it clear that these two backstabs are kissing cousins, unlike the very different backstab ability thieves have in first edition. Both do the same damage, damage that scales identically. Both require either an ally close by or making an attack under favorable conditions, conditions that are not available all the time. Both are essentially the key to combat success for a rogue; the rogue's combat viability derives entirely from making sneak attacks, under the right conditions.
Let's talk about the differences between these two sneak attacks.
With a little help from my friends: The first condition that allows the use of sneak attacks is having an ally close by. In 3E, the ally has to be flanking. That means the rogue has to be in melee, with an enemy between him and his flanking friend. In 3E, combat maneuverability is trickier, more tactical, and riskier, since you provoke attacks of opportunity whenever you leave a threatened square. It is easier, ironically, to flank a foe in 5E, because in 5E you provoke an opportunity attack only when you move totally out of a hostile creature's reach (not when you are approaching and circling). So in 5E it is easy to walk around a foe, but it does not matter, because flanking does not exist in the game (aside from an optional rule in the 5E DMG that is very rarely used).
For a 5E sneak attack, all you need is another enemy of the target within 5 feet of it. Two charaters (a rogue and a friend) standing side by side is fine. Heck, if you are an arcane trickster rogue, having your familiar on your shoulder is all you need to have an ally within 5 ft, if you are toe-to-toe with the enemy.
But wait! 5E makes it easier still! The rule says your ally has to be within 5 ft of the enemy. It does not say YOU have to be anywhere close by at all! A rogue can fire into melee and deal sneak attack damage so long as an ally is next to the foe. If you have to shoot through your ally's space, there may be a penalty for cover. But if you have a clear shot, you are in like Flynn. There is no penalty for shooting into a melee, in 5E, unlike the standard -4 penalty in 3E.
Pity the 3E rogue: For a 3E rogue, there is no flanking at range, and there is no easy shooting into melee to gain sneak attack damage, regardless of the presence of allies. Flanking is harder to set up than having an ally within five feet of a target (and requires the rogue be in melee range). It is easier to gain advantage than it is to deny an enemy their dex bonus, IMNSHO. And on a critical hit, 5E rogues double their sneak attack damage dice! So bottom line: Rogues have it easier in 5E than in 3E when it comes to sneak attacks.
On the flip side, a 3E rogue can do potentially far more damage in a round, because in 5E, you can only make one sneak attack per round. A high-level bow-wielding 3E rogue with Rapid Shot, greater invisibility, and haste could easily make five attacks a round, and all of them gain sneak attack dice. And heck, for a power gamer, I can imagine getting maybe seven to eight attacks a round ... throwing darts with both hands at +11 BAB plus rapid shot plus haste gets you there. But in advancing to that equivalent level, odds are the 5E rogue has used sneak attack more often, and more consistently, than the 3E rogue.
Raising rogues, curtailing casters: I suppose, if there is a theme here, it is the general philosophy of 5E to power down casters and boost non-casters. Only martial classes get a second attack each round in 5E, and rogues get sneak attacks more easily. But with the 5E mechanic of concentration, casters stop being mega-buffers. You can't be an invisible flying mage any more -- you can be invisible or flying, but not both at the same time. In 3E, a medium-high wizard can easily have five, or even ten buffs all running at the same time. Say, Mage Armor, Endure Elements, Protection from Evil, Resist Energy, False Life, Heroism, Greater Magic Weapon, Fly ... that's only off the top of my head, and only up to level 3. Though a level 9+ wizard is more likely to use Overland Flight. When I played a level 18-20 wizard, almost all my 3rd and 4th level slots were given over to boosting the party's weaponry with Greater Magic Weapon. Can't do that in 5E.
So rogues, enjoy playing 5E, be glad your signature ability is both easier to use and usable more often, and make sure you take full advantage of one of the best combat powers in the game.
12 June 2022 update: I will say, the 3E/Pathfinder arcane trickster has one clear advantage. Being able to make sneak attacks with spells -- like rays, say -- is hella cool. In 3E, the mechanical advantage is that such attacks usually require a ranged touch attack, making them much more likely to hit. That's balanced in 3E by ranged sneak attacks being much harder to set up than melee sneak attacks; in 5E, there are no more touch attacks -- every attack strikes at regular AC, armor and natural armor be damned. [That's another way 5E cuts casters down to size.] Still, I would love to see a 5E feat or option or magic item that let you use sneak attacks with spells that require an attack roll to land. 5E's boosted cantrips would become even more useful in that case.
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