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In D&D 5e using a wizard of the School of Necromancy:

If I cast bestow curse on a monster, then kill it with a crossbow, would it trigger the Grim Harvest feature due to the extra 1d8 damage? Does it matter if the monster had 1 HP?

What about if I cast bestow curse, then hit it with magic missile (and kill it with just 1 missile) - would Grim Harvest trigger off the missile or the curse?

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Grim Harvest triggers only when a spell kills a creature.

Grim Harvest reads:

when you kill one or more creatures with a spell of 1st level or higher, you regain hit points equal to twice the spell’s level

Bestow Curse reads:

your attacks and spells deal an extra 1d8 necrotic damage

So to your first question, the 1d8 necrotic damage is added to your attack, so it is not considered damage from the spell, it is from your attack.

To your second question, the 1d8 necrotic is added to the damage of Magic Missile, a spell, so Grim Harvest would trigger based on the level you cast Magic Missile at (assuming it killed its target).

The easy way to remember it is:

Bestow Curse does not deal damage, so it cannot reduce a target's hitpoints to zero.

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    \$\begingroup\$ Thanks for the clarification. It makes a lot of sense. \$\endgroup\$ – Sour Jun 17 at 19:24

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