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We already know from Sage Advice and other answers to other questions that by RAI, (and I guess RAW too), Cutting Words (and Bane) don't work on critical hits, though in the case of Cutting Words they can still reduce the damage by an amount.

The Grave Domain's 6th level feature, Sentinel at Death's Door states that:

As a reaction when you or a creature you can see within 30 feet of you suffers a critical hit, you can turn that hit into a normal hit. Any effects triggered by a critical hit are canceled.

Does that mean that, since it is no longer a critical hit, that Cutting Words can now apply to it properly?

A follow up question: If the above is true then if a Bard cast Cutting Words before the Cleric used Sentinel at Death's Door on a critical hit, does Cutting Words still apply?

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Cutting Words wouldn't be able to affect the attack, only the resulting damage.

Cutting Words' timing is specified with regard to the three things you can use it on: attack rolls, ability checks,

You can choose to use this feature after the creature makes its roll, but before the DM determines whether the attack roll or ability check succeeds or fails,

and damage rolls:

or before the creature deals its damage.

If it was not split up like this (i.e. if the timing for Cutting a damage roll could apply to Cutting an attack roll), there would be no point to having a timing specified for attack rolls at all, because the damage roll timing would render it obsolete.

That out of the way, trying to use Cutting Words in conjunction with Sentinel at Death's Door against the attack would fail no matter what the timing:

  • If used against a natural 20 on an attack roll before Sentinel at Death's Door is used, it's useless, because the attack is still a critical hit even after Cutting Words. (Normal hits that become critical hits upon hitting, through something like Assassinate, could be Cut, but that wouldn't involve Sentinel at Death's Door.)
  • If used after Sentinel at Death's Door against the resulting normal hit, the outcome of the attack roll has already been resolved as a normal hit, which is too late for Cutting Words to affect the attack roll.

Using it on the damage roll, however, is still an option and does work together with Sentinel at Death's Door.

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The grave cleric's ability makes the attack a hit.

It doesn't make the attack a hit if the attack roll remains good enough; the attack roll is now irrelevant.

This is the same reason why changing the attack roll on a critical hit is irrelevant. You can take the natural 20+7 attack and subtract 700 from it, and it remains a critical hit.

After the grave cleric is done, it is a natural 20+7 that is a normal hit. Subtracting 700 from it, it remains a normal hit.

Imagine an ability that reads:

As a reaction, when a creature rolls a 7 on an d20 for an attack roll, you can turn that attack into a hit.

Subtracting 1d8 from the roll wouldn't do anything here.

Similarly, the Grave Cleric turns the Critical Hit into a Hit. It remains a Hit regardless of what the total of the attack roll is. Subtracting 1d8 from the attack roll is possible, but it doesn't do anything of use, unless there is some other thing triggered by the attack roll total besides "does it hit".

Feel free to apply Cutting Words to the attack roll, but it just won't help.

Note that you can apply Cutting Words to a Critical Hit even without the Grave Cleric; but, just as with the Grave Cleric case, it doesn't do anything of use. The attack is a Critical Hit, subtracting 1d8 from the attack roll doesn't make it not a Critical Hit.

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It depends on the concept of an "automatic hit".

From Does a natural 20 on the attack roll still automatically hit if the target is wearing adamantine armor? and Sage Advice:

Q: Does the nat 20 still auto hit against adamantine armor?

A: Yes.

This suggests there are four possible results from an attack roll:

  1. a critical hit (doubles damage dice)
  2. an automatic hit (can't be turned into a miss by features like bane and Cutting Words)
  3. a hit (dice + attack bonuses - attack penalties >= target's armor class), and
  4. a miss.

In this case, Sentinel at Death's Door turns the critical hit into an automatic hit, which can't be turned into a miss by any features or penalties.

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