I have seen several people say that a weapon "Of Life Stealing" only gets the bonus damage and Temp. HP when you roll a Natural 20 on the die used to make the attack. If you just look at the weapon description, you can see why people may say this. I however disagree and think so long as the total of the Attack roll is 20+ it will work. I would like some clarification from someone with authority on game rules.
A magical weapon with the "Life Stealing" ability generally reads as follows:
"When you Attack a creature with this Magic Weapon and roll a 20 on the Attack roll, that target takes an extra 3d6 necrotic damage, provided that the target isn’t a construct or an Undead. You gain temporary Hit Points equal to the extra damage dealt."
Notice how it says "Roll a 20 on the Attack roll". According to both the Basic Rule and the PHB, an Attack roll is the following:
"When you make an attack, your attack roll determines whether the attack hits or misses. To make an attack roll, roll a d20 and add the appropriate modifiers. If the total of the roll plus modifiers equals or exceeds the target's Armor Class (AC), the attack hits. The AC of a character is determined at character creation. whereas the AC of a monster is in its stat block."
"To make an Attack roll, roll a d20 andadd the appropriate modifiers". Both the Basic Rules and the PHB has the following to say about Nat 1's & 20's:
"Sometimes fate blesses or curses a combatant, causing the novice to hit and the veteran to miss. If the d20 roll for an attack is a 20, the attack hits regardless of any modifiers or the target's AC. In addition, the attack is a critical hit, as explained later in this chapter. If the d20 roll for an attack is a I, the attack misses regardless of any modifiers or the target's AC."
Notice how this section says "If the d20roll for an attack is a 20, the attack hits regardless of any modifiers". Another thing to note is that weapon with the "Life Stealing" ability do not say "20 or more". I'd like a definitive answer on how these weapons work.
Even if you interpret the text on Sword of Life Stealing to mean the total, including modifiers, it would still not trigger on a "natural 19, with a +2 bonus", because that would be 21, not 20. So it would still be a 5% chance of occurring, as long as the total modifier is between 0 and 19 (with a negative modifier, or a modifier higher than +20 (which is, as far as I know, unattainable), it is impossible to roll a modified 20). The intent, though, is pretty clearly to have the effect go off on natural 20's, regardless of modifiers.
I agree with Tonio. The intent clearly is that it only apply with a natural 20 on the die. Since it says 20 on the attack roll, not 20 or higher, your tortured reading would mean it would only trigger on a number determined by your modifiers, so a natural 15 might trigger it, but a 20 would not.
If the point is that it works on a natural 20, do you mean specifically a critical hit or a literal natural 20, what happens if you play a Champion Fighter, does improved critical count?
If the point is that it works on a natural 20, do you mean specifically a critical hit or a literal natural 20, what happens if you play a Champion Fighter, does improved critical count?
It says "roll a 20" so it would have to be a natural 20 not just any critical hit, unless the DM rules in your favor.
If the point is that it works on a natural 20, do you mean specifically a critical hit or a literal natural 20, what happens if you play a Champion Fighter, does improved critical count?
I'm guessing if they meant "critical hit", they would've said "critical hit". So no, a Champion rolling a 19 would not trigger it, but a creature wielding the Sword of Life Stealing rolling a natural 20 when hitting a target with Adamantine Armorwould trigger it.
If the point is that it works on a natural 20, do you mean specifically a critical hit or a literal natural 20, what happens if you play a Champion Fighter, does improved critical count?
When they're explicit about a number, be it a die roll or a distance, they mean exactly that. Contrast it with the Great Weapon Master feat, which says you can make an additional attack as a Bonus Action if you a) drop an enemy to 0 HP or b) land a critical hit. They didn't say b) roll a natural 20. Therefore, any way you're able to land a crit will work(as a Champion rolling a nat19, hitting someone under the effect of a Sleep spell, etc)
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I have seen several people say that a weapon "Of Life Stealing" only gets the bonus damage and Temp. HP when you roll a Natural 20 on the die used to make the attack. If you just look at the weapon description, you can see why people may say this. I however disagree and think so long as the total of the Attack roll is 20+ it will work. I would like some clarification from someone with authority on game rules.
A magical weapon with the "Life Stealing" ability generally reads as follows:
"When you Attack a creature with this Magic Weapon and roll a 20 on the Attack roll, that target takes an extra 3d6 necrotic damage, provided that the target isn’t a construct or an Undead. You gain temporary Hit Points equal to the extra damage dealt."
Notice how it says "Roll a 20 on the Attack roll". According to both the Basic Rule and the PHB, an Attack roll is the following:
"When you make an attack, your attack roll determines whether the attack hits or misses. To make an attack roll, roll a d20 and add the appropriate modifiers. If the total of the roll plus modifiers equals or exceeds the target's Armor Class (AC), the attack hits. The AC of a character is determined at character creation. whereas the AC of a monster is in its stat block."
"To make an Attack roll, roll a d20 and add the appropriate modifiers". Both the Basic Rules and the PHB has the following to say about Nat 1's & 20's:
"Sometimes fate blesses or curses a combatant, causing the novice to hit and the veteran to miss. If the d20 roll for an attack is a 20, the attack hits regardless of any modifiers or the target's AC. In addition, the attack is a critical hit, as explained later in this chapter. If the d20 roll for an attack is a I, the attack misses regardless of any modifiers or the target's AC."
Notice how this section says "If the d20 roll for an attack is a 20, the attack hits regardless of any modifiers". Another thing to note is that weapon with the "Life Stealing" ability do not say "20 or more". I'd like a definitive answer on how these weapons work.

Even if you interpret the text on Sword of Life Stealing to mean the total, including modifiers, it would still not trigger on a "natural 19, with a +2 bonus", because that would be 21, not 20. So it would still be a 5% chance of occurring, as long as the total modifier is between 0 and 19 (with a negative modifier, or a modifier higher than +20 (which is, as far as I know, unattainable), it is impossible to roll a modified 20). The intent, though, is pretty clearly to have the effect go off on natural 20's, regardless of modifiers.
I agree with Tonio. The intent clearly is that it only apply with a natural 20 on the die. Since it says 20 on the attack roll, not 20 or higher, your tortured reading would mean it would only trigger on a number determined by your modifiers, so a natural 15 might trigger it, but a 20 would not.
If the point is that it works on a natural 20, do you mean specifically a critical hit or a literal natural 20, what happens if you play a Champion Fighter, does improved critical count?
It says "roll a 20" so it would have to be a natural 20 not just any critical hit, unless the DM rules in your favor.
I'm guessing if they meant "critical hit", they would've said "critical hit". So no, a Champion rolling a 19 would not trigger it, but a creature wielding the Sword of Life Stealing rolling a natural 20 when hitting a target with Adamantine Armor would trigger it.
When they're explicit about a number, be it a die roll or a distance, they mean exactly that. Contrast it with the Great Weapon Master feat, which says you can make an additional attack as a Bonus Action if you a) drop an enemy to 0 HP or b) land a critical hit. They didn't say b) roll a natural 20. Therefore, any way you're able to land a crit will work(as a Champion rolling a nat19, hitting someone under the effect of a Sleep spell, etc)