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Expanding upon this question in a tweet at Jeremy Crawford who confirms once again that Initiative is a skill check and can be modified by things that modify ability checks.

Cutting Words states

When a creature that you can see within 60 feet of you makes an attack roll, an ability check, or a damage roll, you can use your reaction to expend one of your uses of Bardic Inspiration, rolling a Bardic Inspiration die and subtracting the number rolled from the creature’s roll.

Can a reaction be used to influence the result of an enemies Initiative roll or does the existence of a reaction necessitate being in combat?

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    \$\begingroup\$ If this is possible, it opens up the secondary question of if you then have an actual reaction in combat until your turn arrives, or not. \$\endgroup\$ – SeriousBri Jul 1 at 11:17
  • \$\begingroup\$ @Tiggerous I assume the worry is that you get a reaction before your first turn, and one on/after your first turn, inflating the action economy of the combat by 1 turnless reaction. \$\endgroup\$ – Akixkisu Jul 1 at 12:28
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You can use a reaction to affect initiative rolls.

Initiative (PHB 177):

At the beginning of every combat, you roll initiative by making a Dexterity check.

You would automatically become part of the combat, but there is not a single instance, in the rules, that necessitates that you can't start the combat with a reaction with the usual exception of Surprise (PHB 189):

If you’re surprised, you can’t move or take an action on your first turn of the combat, and you can’t take a reaction until that turn ends.

Reactions (PHB 190):

Certain special abilities, spells, and situations allow you to take a special action called a reaction. A reaction is an instant response to a trigger of some kind, which can occur on your turn or on someone else’s.

If you worded the trigger correctly, you would intervene in the combat and therefore would have to roll initiative.

Initiative (PHB 189):

When combat starts, every participant makes a Dexterity check to determine their place in the initiative order.

You couldn't take another reaction before it is your turn.

When you take a reaction, you can’t take another one until the start of your next turn. If the reaction interrupts another creature’s turn, that creature can continue its turn right after the reaction.

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    \$\begingroup\$ "If you worded the trigger correctly" - in the case of Cutting Words, the trigger is a creature the Bard can see making a roll (here, an ability check). This doesn't require a previous Ready action, and there's nothing to be "worded". \$\endgroup\$ – aschepler Jul 2 at 4:57
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No, because it's not anyone's turn.

Certain special abilities, spells, and situations allow you to take a special action called a reaction. A reaction is an instant response to a trigger of some kind, which can occur on your turn or on someone else’s.

Now, we don't normally keep track of turns out of combat, but if someone is trying to take some effective action that involves an ability check, then in some sense they're taking a turn, and you can use your Cutting Words to try to mess them up.

But initiative is special--it's an ability check that everyone makes at the same time to decide the turn order, which means the turn order hasn't been decided yet and so it is neither your turn nor anyone else's.

Diegetically, this reflects the fact that if someone else is quicker to make the first move than you are, you can't negate that by making the second move. They already beat you. Whatever the bard actually does when using Cutting Words, he can't do it until he realizes it's time to do something.

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  • \$\begingroup\$ Comments are not for extended discussion; this conversation has been moved to chat. \$\endgroup\$ – Rubiksmoose Jul 2 at 19:07
  • \$\begingroup\$ I think your argument maybe helped by putting up the official definition of “turn”. You state that prior to initiative there are no turns so explain what is a turn. \$\endgroup\$ – MivaScott Jul 2 at 20:31
  • \$\begingroup\$ I don't think it's correct to say that you can't take reactions when you are out of combat. A common-sense reading of the Feather Fall spell would allow you to cast it when you accidentally set off a pit trap, for example. There's nothing special about the Initiative check - indeed it's a regular ability check that can be affected by Jack Of All Trades and Enhance Ability - so you'd only be unable to use a reaction to affect it if you were Surprised (which is determined before initiative is rolled and would prevent you from taking the reaction). \$\endgroup\$ – dhmstark Jul 4 at 20:15

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