Can you apply more than one Sword of Wounding wound per round?

Question

The description for Sword of Wounding states the following:

Once per turn, when you hit a creature with an attack using this magic weapon, you can wound the target. At the start of each of the wounded creature’s turns, it takes 1d4 necrotic damage for each time you’ve wounded it.

"Once per turn" in the description seems to imply that only a single wound can be applied at a time before the damage triggers. As such, the total damage inflicted by this effect seems like it would be relatively small due to the low maximum number of wounds that can be inflicted in a typical combat encounter.

Are there any ways to apply this effect more than once per round in order to increase its effectiveness?

Answer 1

Yes you can.

Normally, game features with the same name do not stack on one target, the rule for Combining Game Effects states:

Different game features can affect a target at the same time. But when two or more game features have the same name, only the effects of one of them—the most potent one—apply while the durations of the effects overlap.

However, D&D 5e has a specific-beats-general rule, which states:

many racial traits, class features, spells, magic items, monster abilities, and other game elements break the general rules in some way, creating an exception to how the rest of the game works. Remember this: If a specific rule contradicts a general rule, the specific rule wins.

The Sword of Wounding creates one such exception:

At the start of each of the wounded creature’s turns, it takes 1d4 necrotic damage for each time you’ve wounded it.

The phrase "for each time you've wounded it" indicates that the wounding effect of the sword can stack on one target, which is an exception to the "same name doesn't stack" rule quoted above.

Finally, since the Sword of Wounding's effect is limited to "once per turn", not once per round, as long as you have a method of attacking on two or more turns in a round (usually your own turn and another turn via opportunity attack or other reaction-granting feature), you can impose the wounding effect on the same creature twice in one round (or more if some feature allows you to make more attacks on more turns).

Answer 2

Yes!

Importantly, the description does not state "once on your turn" (which would definitely limit the number of uses of this effect to once per round). Instead, it states "once per turn", which means that this effect can be applied once on any turn in a round, provided you are able to land an attack during that turn.

As such, any effect which allows you to attack outside of your own turn will allow you to stack this effect. The most common way would be via an opportunity attack, as this occurs on the instigators turn.

This is essentially the same problem that Rogues contend with when using their Sneak Attack, which uses similar verbiage. This answer demonstrates that the upper limit of uses per round for an effect of this type is, in fact, the number of turns in a round.

Answer 3

Yes! And even more than that!

So, as others have mentioned, it's once per turn rather than once per round. That's great, and will certainly help you bump your numbers, but it's also once per turn "using this magic weapon". You can dual-wield swords of wounding, hit them one or more times with each, and rack up the wounds even faster.

It's also taking that damage at the start of every one of its turns. Think of it as a form of extra damage. If it only lives until its next round, you did 1d4 extra damage. If it lives for two more, it did 2d4. If it lives for three, 3d4... except for the savign throw, which ends it. The save effectively cuts it down to max 2d4 per wound, reduced further by the chance that he'll die before your saves go in. for a rare sword... well, Flame Blade is also rare, deals 2d6 fire when aflame, and provides a light source. Mostly, I think that the answer is that the wounding blade is decent, but not great.