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While DnD 5e no longer includes flanking as a standard rule, they have an optional rule that covers it. I've not played earlier versions, but I imagine it's very similar (if not identical) to the standard rule that existed in earlier versions. Here is the optional flanking rule from DMG p. 251:

When a creature and at least one of its allies are adjacent to an enemy and on opposite sides or corners of the enemy's space, they flank that enemy, and each of them has advantage on melee attack rolls against that enemy. - (DMG p. 251)

So if a medium creature (taking up just one square) has three adjacent enemies, two of whom are on opposite sides or corners, do all three have advantage, or just the two who are flanking?

  A            B        A
B T   OR   A T A   OR   B T
  A                         A   etc.

Where "A" and "B" are allies and "T" is the target creature.

In each of these examples, "B" is not causing the target creature to be flanked, as there isn't another creature on the opposite side to "T" from it. Does B still get advantage?

Put another way, could we say that if a creature is flanked (see above) then all melee attacks against them are made with advantage? Or would it be better to say if "they flank that enemy, [...] both of them [have] advantage on melee attack rolls?"

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When dealing with Medium creatures, yes, it might read more easily to say "both". The "each of them" becomes important when dealing with Large or bigger creatures, which take up so much space that multiple creatures can fit side by side on one end.

The rule, from the viewpoint of the attacker, is basically:

  • Am I adjacent to an enemy?
  • Is at least one of my allies also adjacent to the creature on the opposite end?

If yes, you have flanking.

For an example of when the "each" comes into play, see below diagram of three Allies flanking a Giant. In this situation, all three Allies attack with advantage due to flanking, because "Am I adjacent to an enemy and is there an ally adjacent on the opposite of the creature" is true for all three.

A A

G G

G G

A

On the other hand, in this situation, that doesn't work.

A

G G A

G G

A

While the top and bottom attacker have advantage due to flanking, the one on the right does not.

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Only the A's are flanking.

When a creature and at least one of its allies are adjacent to an enemy and on opposite sides or corners of the enemy's space, they flank that enemy, and each of them has advantage on melee attack rolls against that enemy. - (DMG p. 251)

  • By the grammar of the sentence "each of them" refers to the two allies which are flanking. There is no reference to any additional allies in the entire passage, nor is it written in a way which would imply that while being flanked, the creature has taken on a conditional status.
  • It is specifically the 'flankers' who gain a conditional status and subsequently now have an advantage bonus, if-and-only-if: they are uniquely positioned to flank (by being on opposite sides).
  • Furthermore, this interpretation is backed up by previous editions of D&D.
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I like to think of it in terms of real combat. If you have an enemy in front of you, and one to the side, you're distracted by both enemies attacking you. This gives the attackers an advantage. This advantage becomes even greater when you're being attacked on opposite sides.

The same could be argued for a ranged enemy attacking you from a distance while you have another in front of you, especially if you are not aware of said opponent. This can be true even if they are standing in front of you. It just depends on how distracted you are.

In the game, Final Fantasy Tactics, players are rewarded with higher hit rates when attacking from the side and especially from behind (for example: 60% hit rate from the front, 75% from the side, and 90% from behind). The game is particular, in that it even gives the players the option of selecting which way to face, when ending their turn. I have seen this in other games, as well.

But this is DnD, and things are not so easy as a computer program. Perhaps attacks from the side (when there is an ally presently attacking your target) can be given a +1, rather than advantage? It's up to the DM to decide, but I think there is merit in the argument that an opponent is at least somewhat distracted when being attacked by two or more enemies.

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  • 2
    \$\begingroup\$ Welcome to the site! Please take the tour when you get the chance. The asker is specifically asking whether, according to the optional flanking rules, melee attackers who do not have an ally opposite them still gain advantage for attacking a target that is flanked by other allies. You've got an interesting answer here, but it would benefit from directly answering the original question. You can edit your answer by clicking the edit button at the lower left of it. \$\endgroup\$ – Oblivious Sage Sep 12 '18 at 18:50

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