5th Edition’s flanking optional rule grants advantage to Player Characters who are on opposite sides of a foe. We’ve previously focused on 5e flanking, including examining what feat(ures) it overlaps, how to manage it in relation to the tactical environments of your game, and some alternate suggestions for how to handle it (e.g. +2 attack, no flanking if flanked).
There’s another possibility we didn’t explore. While that’s not without reason, it does provide an interesting design exercise.
What if flanking gave a bonus to damage?
How to Do It?
There’s a few methods you could use to apply this idea:
- Add a flat damage bonus to a successful flanking attack.
- Add an extra weapon die to a successful flanking attack.
- Add a damage die to a successful flanking attack.
- Add scaling sneak attack dice to a successful flanking attack.
- Add extra damage dice for each flanking ally.
- Scaled by…
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DDOCentral 
IMC, we use “flanking grants advantage”, and “can’t flank (or provide flanking) if you’re flanked (or blind/prone/stunned/incapacitated/restrained)”. The Rogue is generally firing from stealth, or is one of the flankers; sometimes, thanks to Tasha, standing still for Steady Aim sneak attacks. Flanking is generally a very ideal circumstance – and, coming from 4e, we’re very comfortable with a tactical grid – and is always sought if possible.
I think giving bonus damage is probably too much on top of this. It would just be saying “Everyone, do an extra Xd6 on every attack. Except you, wizard; you lose.”
HOWEVER, what I don’t have a happy solution for is “Flanking when you already have Advantage”. You discussed this – and I commented – in your other article. In my houserules, I decided “you get an extra +2 to hit”. Has never been used in practice. Maybe the answer is, instead, this Flanking Damage bonus. If you already have advantage, and you flank the target, you’re not only more likely to land a hit, you’re more likely to land a solid blow. Maybe *that’s* when you add the +1d6. Sure, the Rogue can Sneak Attack for +Xd6 (nearly) all the time, but the fighter can land those nasty hits too, if he’s flanked a target and then knocks it prone for the extra d6! Or maybe the wizard has restrained the foe in a Maximilian’s Stony Grasp, and the cleric steps up to flank, and lands a solid ribcracker (+d6) with his hammer.
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