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If a monster has an attack with two targets. Do I make a separate attack roll for each player, or do I make one attack roll and compare to each AC individually?

The monster in question , from A Wild Sheep Chase, has the following stat:

Whirling Greatsword Melee Weapon Attack +5 to hit, reach 5 ft. Two seperate[sic] targets. Hit: 10 [2d6+3) slashing damage.

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  • \$\begingroup\$ What is the other option? \$\endgroup\$
    – enkryptor
    Apr 22, 2020 at 18:25
  • \$\begingroup\$ Are you asking how to choose its targets? \$\endgroup\$
    – Mark Wells
    Apr 22, 2020 at 18:27
  • \$\begingroup\$ To clarify: is the question "Do I make a separate attack roll for each player, or do I make one attack roll and compare to each AC individually"? \$\endgroup\$
    – Carcosa
    Apr 22, 2020 at 18:40
  • \$\begingroup\$ I'm not sure what exactly is unclear here. \$\endgroup\$
    – Mołot
    Apr 22, 2020 at 18:41
  • \$\begingroup\$ @Corcosa yes, that is the thing that is unclear I think. \$\endgroup\$
    – Ralph
    Apr 22, 2020 at 18:42

2 Answers 2

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It isn't clear

Unfortunately, this is a homebrew that doesn't use standard language, which means the "true" answer is something only the creator can say.

But there may be a hint.

Whirlwind

The attack uses the term Whirlwind, which is also the name of a ranger mechanic that says:

You can use your action to make a melee attack against any number of creatures within 5 feet of you, with a separate attack roll for each target.

This may have been the mechanic that inspired the homebrew. If so, then you'd roll separately.

But unfortunately, the final decision lies with either the creator or the DM (if that's just, you can make a call either way.) We can't tell you for certain.

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The best-supported interpretation is a single attack roll and one to two targets.

It seems to be a homebrew creature with its attack description written in a non-standard style.

This is odd because a lack of comparable text in official sources makes it hard to resolve ambiguities in this specific case. The prevailing 5e guideline is to interpret what is written as directly as possible. Applying that here would suggest:

  • One single attack roll

If the attack description said make two rolls, you would make two rolls. It doesn't, so this is a single-attack action. Additionally, the stat block for Guz does not include a multiattack option, so this is not a case of a creature getting to make two distinct attacks as part of a single Attack action.

  • which can hit two different targets

It explicitly describes two distinct targets (so you can't hit the same target twice with the one attack), so the single attack roll would be compared to each target's AC to determine a hit for that target.

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