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?
Best Answer
Yes you can.
Normally, game features with the same name do not stack on one target, the rule for Combining Game Effects states:
However, D&D 5e has a specific-beats-general rule, which states:
The Sword of Wounding creates one such exception:
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).